Table of Contents
Journal of Catalysts
Volume 2013 (2013), Article ID 614829, 20 pages
http://dx.doi.org/10.1155/2013/614829
Review Article

Solid-Phase Organic Synthesis and Catalysis: Some Recent Strategies Using Alumina, Silica, and Polyionic Resins

Department of Chemistry, University of North Bengal, Darjeeling 734 013, India

Received 26 February 2013; Accepted 7 July 2013

Academic Editor: Raghunath V. Chaudhari

Copyright © 2013 Basudeb Basu and Susmita Paul. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. B. Merrifield, “Solid phase peptide synthesis. I. The synthesis of a tetrapeptide,” Journal of the American Chemical Society, vol. 85, no. 14, pp. 2149–2154, 1963. View at Publisher · View at Google Scholar
  2. G. H. Posner, “Organic reactions at alumina surfaces,” Angewandte Chemie—International Edition, vol. 17, no. 7, pp. 487–496, 1978. View at Google Scholar
  3. A. McKillop and K. W. Young, “Organic synthesis using supported reagents—part I & part II,” Synthesis, pp. 401–422, 481–500, 1979. View at Google Scholar
  4. A. Cornelis and P. Laszlo, “Clay-supported copper(II) and iron(III) nitrates: novel multi-purpose reagents for organic synthesis,” Synthesis, no. 10, pp. 909–918, 1985. View at Publisher · View at Google Scholar
  5. P. Laszlo, Preparative Chemistry Using Supported Reagents, Academic Press, San Diego, Calif, USA, 1987.
  6. E. K. Smith, Solid Supports and Catalyst in Organic Synthesis, Ellis Horwood, Chichester, UK, 1992.
  7. M. Balogh and P. Laszlo, Organic Chemistry Using Clays, Springer, Berlin, Germany, 1993.
  8. J. H. Clark, Catalysis of Organic Reactions by Supported Inorganic Reagents, VCH, New York, NY, USA, 1994.
  9. R. L. Letsinger and V. Mahadevan, “Oligonucleotide synthesis on a polymer support,” Journal of the American Chemical Society, vol. 87, no. 15, pp. 3526–3527, 1965. View at Google Scholar · View at Scopus
  10. J. M. Fraile, J. A. Mayoral, A. J. Royo et al., “Supported chiral amino alcohols and diols functionalized with aluminium and titanium as catalysts of Diels-Alder reaction,” Tetrahedron, vol. 52, no. 29, pp. 9853–9862, 1996. View at Publisher · View at Google Scholar · View at Scopus
  11. A. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford Science Publications, New York, NY, USA, 1998.
  12. P. T. Anastas and T. Williamson, Green Chemistry: Frontiers in Benign Chemical Synthesis and Procedures, Oxford Science Publications, New York, NY, USA, 1998.
  13. J. H. Clark, “Green chemistry: challenges and opportunities,” Green Chemistry, vol. 1, no. 1, pp. 1–8, 1999. View at Publisher · View at Google Scholar
  14. M. Lancaster, Green Chemistry: An Introductory Text, Royal Society of Chemistry, Cambridge, Mass, USA, 2002.
  15. G. W. V. Cave, C. L. Raston, and J. L. Scott, “Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility,” Chemical Communications, no. 21, pp. 2159–2169, 2001. View at Google Scholar · View at Scopus
  16. P. Hodge and D. C. Sherrington, Polymer-Supported Reactions in Organic Synthesis, John Wiley and Sons, Chichester, UK, 1980.
  17. P. Hodge and D. C. Sherrington, Syntheses and Separations Using Functional Polymers, John Wiley and Sons, Chichester, UK, 1988.
  18. A. Akelah and D. C. Sherrington, “Recent developments in the application of functionalized polymers in organic synthesis,” Polymer, vol. 24, no. 11, pp. 1369–1386, 1983. View at Publisher · View at Google Scholar
  19. J. A. Gladysz, “Introduction: recoverable catalysts and reagents—perspective and prospective,” Chemical Reviews, vol. 102, no. 10, pp. 3215–3216, 2002. View at Publisher · View at Google Scholar · View at Scopus
  20. D. C. Sherrington, “Polymer-supported reagents, catalysts, and sorbents: evolution and exploitation—a personalized view,” Journal of Polymer Science, Part A, vol. 39, no. 14, pp. 2364–2377, 2001. View at Publisher · View at Google Scholar · View at Scopus
  21. D. C. Sherrington, “Preparation, structure and morphology of polymer supports,” Chemical Communications, no. 21, pp. 2275–2286, 1998. View at Google Scholar · View at Scopus
  22. P. Wentworth and K. D. Janda, “Liquid-phase chemistry: recent advances in soluble polymer-supported catalysts, reagents and synthesis,” Chemical Communications, no. 19, pp. 1917–1924, 1999. View at Google Scholar
  23. J. S. Yadav and H. M. Meshram, “Green twist to an old theme. An eco-friendly approach,” Pure and Applied Chemistry, vol. 73, no. 1, pp. 199–203, 2001. View at Google Scholar · View at Scopus
  24. M. Lebl, “Solid-phase synthesis on planar supports,” Biopolymers, vol. 47, pp. 397–404, 1998. View at Google Scholar
  25. N. J. Maeji, R. M. Valerio, A. M. Bray, R. A. Campbell, and H. M. Geysen, “Grafted supports used with the multipin method of peptide synthesis,” Reactive Polymers, vol. 22, no. 3, pp. 203–212, 1994. View at Google Scholar · View at Scopus
  26. N. Hird, I. Hughes, D. Hunter, M. G. J. T. Morrison, D. C. Sherrington, and L. Stevenson, “Polymer discs—an alternative support format for solid phase synthesis,” Tetrahedron, vol. 55, no. 31, pp. 9575–9584, 1999. View at Publisher · View at Google Scholar · View at Scopus
  27. R. C. D. Brown, “Recent developments in solid-phase organic synthesis,” Journal of the Chemical Society, Perkin Transactions 1, no. 19, pp. 3293–3320, 1998. View at Publisher · View at Google Scholar
  28. D. C. Sherrington, “Polymer-supported synthesis,” in Chemistry of Waste Minimisation, J. H. Clark, Ed., chapter 6, Blackie Academic, London, UK, 1995. View at Google Scholar
  29. J. H. Clark, A. P. Kybett, and D. J. Macquarrie, Supported Reagents: Preparation, Analysis and Applications, VCH, New York, NY, USA, 1992.
  30. D. J. Gravert and K. D. Janda, “Organic synthesis on soluble polymer supports: liquid-phase methodologies,” Chemical Reviews, vol. 97, no. 2, pp. 489–509, 1997. View at Google Scholar · View at Scopus
  31. J. O. Metzger, “Solvent-free organic syntheses,” Angewandte Chemie—International Edition, vol. 37, no. 21, pp. 2975–2978, 1998. View at Google Scholar
  32. M. S. Singh and S. Chowdhury, “Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis,” RSC Advances, vol. 2, no. 11, pp. 4547–4592, 2012. View at Publisher · View at Google Scholar
  33. K. Tanaka, Solvent-Free Organic Synthesis, Wiley-VCH GmbH & Co. KGaA, Weinheim, Germany, 2003.
  34. R. S. Varma, “Solvent-free organic syntheses using supported reagents and microwave irradiation,” Green Chemistry, vol. 1, no. 1, pp. 43–55, 1999. View at Publisher · View at Google Scholar
  35. R. S. Varma, “Solvent-free accelerated organic syntheses using microwaves,” Pure and Applied Chemistry, vol. 73, no. 1, pp. 193–198, 2001. View at Publisher · View at Google Scholar
  36. M. H. Sarvari and H. Sharghi, “Zinc oxide (ZnO) as a new, highly efficient, and reusable catalyst for acylation of alcohols, phenols and amines under solvent free conditions,” Tetrahedron, vol. 61, no. 46, pp. 10903–10907, 2005. View at Publisher · View at Google Scholar · View at Scopus
  37. K. Wilson and J. H. Clark, “Solid acids and their use as environmentally friendly catalysts in organic synthesis,” Pure and Applied Chemistry, vol. 72, no. 7, pp. 1313–1319, 2000. View at Publisher · View at Google Scholar
  38. A. Loupy, “Solvent-free reactions,” Topics in Current Chemistry, vol. 206, pp. 153–207, 1999. View at Publisher · View at Google Scholar
  39. R. H. Andreatta and H. Rink, “Zur problematik der peptidsynthese an tragern: beitrag eines neuen Verfahrens mit loslichen tragern,” Helvetica Chimica Acta, vol. 56, no. 4, pp. 1205–1218, 1973. View at Publisher · View at Google Scholar
  40. M. M. Shemyakin, Y. A. Ovchinnikov, A. A. Kinyushkin, and I. V. Kozhevnikova, “Synthesis of peptides in solution on a polymeric support I. Synthesis of glycylglycyl-l-leucylglycine,” Tetrahedron Letters, vol. 6, no. 27, pp. 2323–2327, 1965. View at Google Scholar · View at Scopus
  41. S. H. L. Chiu and L. Anderson, “Oligosaccharide synthesis by the thioglycoside scheme on soluble and insoluble polystyrene supports,” Carbohydrate Research, vol. 50, no. 2, pp. 227–238, 1976. View at Publisher · View at Google Scholar
  42. S. Chert and K. D. Janda, “Synthesis of prostaglandin E2 methyl ester on a soluble-polymer support for the construction of prostanoid libraries,” Journal of the American Chemical Society, vol. 119, no. 37, pp. 8724–8725, 1997. View at Publisher · View at Google Scholar
  43. H. Hayatsu and H. G. Khorana, “Studies on polynucleotides. LXXII. Deoxyribooligonucleotide synthesis on a polymer support,” Journal of the American Chemical Society, vol. 89, no. 15, pp. 3880–3887, 1967. View at Google Scholar · View at Scopus
  44. M. Narita, “Liquid phase peptide synthesis by the fragment condensation on soluble polymer support. I. Efficient coupling and relative reactivity of a peptide fragment with various coupling reagents,” Bulletin of the Chemical Society of Japan, vol. 51, no. 5, pp. 1477–1480, 1978. View at Publisher · View at Google Scholar
  45. E. Cramer, R. Helbig, H. Hettler, K. H. Scheit, and H. Seliger, “Oligonucleotid-Synthese an einem löslichen Polymeren als Träger,” Angewandte Chemie, vol. 78, no. 12, pp. 640–641, 1966. View at Publisher · View at Google Scholar
  46. R. L. Letsinger and M. J. Kornet, “Popcorn polymer as a support in multistep syntheses,” Journal of the American Chemical Society, vol. 85, no. 19, pp. 3045–3046, 1963. View at Google Scholar · View at Scopus
  47. A. Guyot, “Polymer supports with high accessibility,” Pure and Applied Chemistry, vol. 60, no. 3, pp. 365–376, 1988. View at Publisher · View at Google Scholar
  48. F. Svec and J. M. J. Frchet, “New designs of macroporous polymers and supports: from separation to biocatalysis,” Science, vol. 273, no. 5272, pp. 205–211, 1996. View at Publisher · View at Google Scholar
  49. M. Hori, D. J. Gravert, R. Wentworth, and K. D. Janda, “Investigating highly crosslinked macroporous resins for solid-phase synthesis,” Bioorganic & Medicinal Chemistry Letters, vol. 8, no. 17, pp. 2363–2368, 1998. View at Publisher · View at Google Scholar
  50. E. R. L. Malenfant and J. M. J. Frchet, “The first solid-phase synthesis of oligothiophenes,” Chemical Communications, no. 23, pp. 2657–2658, 1998. View at Publisher · View at Google Scholar
  51. G. W. Kabalka and R. M. Pagni, “Organic reactions on alumina,” Tetrahedron, vol. 53, no. 24, pp. 7999–8065, 1997. View at Publisher · View at Google Scholar · View at Scopus
  52. B. Basu and B. Mandal, “KF/alumina: a potential heterogeneous base for organic reactions,” Current Organic Chemistry, vol. 15, no. 22, pp. 3870–3893, 2011. View at Publisher · View at Google Scholar
  53. T. Ando, S. J. Brown, J. H. Clark et al., “Alumina-supported fluoride reagents for organic synthesis: optimisation of reagent preparation and elucidation of the active species,” Journal of the Chemical Society, Perkin Transactions 2, no. 8, pp. 1133–1139, 1986. View at Publisher · View at Google Scholar
  54. T. Ando, J. H. Clark, D. G. Cork, and T. Kimura, “Surface analysis of MF-aluminas and related supported reagents by scanning electron microscopy,” Bulletin of the Chemical Society of Japan, vol. 59, no. 10, pp. 3281–3282, 1986. View at Publisher · View at Google Scholar
  55. T. Ando, J. H. Clark, D. G. Cork, T. Hanafusa, J. Ichihara, and T. Kimura, “Fluoride-alumina reagents: the active basic species,” Tetrahedron Letters, vol. 28, no. 13, pp. 1421–1424, 1987. View at Google Scholar · View at Scopus
  56. J. H. Clark, “Fluoride ion as a base in organic synthesis,” Chemical Reviews, vol. 80, no. 5, pp. 429–452, 1980. View at Publisher · View at Google Scholar
  57. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, and D. Mathé, “New solvent-free organic synthesis using focused microwaves,” Synthesis, no. 9, pp. 1213–1234, 1998. View at Google Scholar · View at Scopus
  58. A. Guram and S. L. Buchwald, “Palladium-catalyzed aromatic aminations with in situ generated aminostannanes,” Journal of the American Chemical Society, vol. 116, no. 17, pp. 7901–7902, 1994. View at Publisher · View at Google Scholar
  59. J. P. Wolfe, S. Wagaw, J.-F. Marcoux, and S. L. Buchwald, “Rational development of practical catalysts for aromatic carbon-nitrogen bond formation,” Accounts of Chemical Research, vol. 31, no. 12, pp. 805–818, 1998. View at Google Scholar · View at Scopus
  60. J. Louie and J. F. Hartwig, “Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents,” Tetrahedron Letters, vol. 36, no. 21, pp. 3609–3612, 1995. View at Publisher · View at Google Scholar · View at Scopus
  61. J. F. Hartwig, “Approaches to catalyst discovery. New carbon-heteroatom and carbon-carbon bond formation,” Pure and Applied Chemistry, vol. 71, no. 8, pp. 1417–1423, 1999. View at Publisher · View at Google Scholar
  62. D. W. Old, J. P. Wolfe, and S. L. Buchwald, “A highly active catalyst for palladium-catalyzed cross-coupling reactions: room-temperature Suzuki couplings and amination of unactivated aryl chlorides,” Journal of the American Chemical Society, vol. 120, no. 37, pp. 9722–9723, 1998. View at Publisher · View at Google Scholar
  63. B. Basu, S. Jha, N. K. Mridha, and M. M. H. Bhuiyan, “Palladium-catalysed amination of halopyridines on a KF-alumina surface,” Tetrahedron Letters, vol. 43, no. 44, pp. 7967–7969, 2002. View at Publisher · View at Google Scholar · View at Scopus
  64. B. Basu, P. Das, A. K. Nanda, S. Das, and S. Sarkar, “Palladium-catalyzed selective amination of haloaromatics on KF-alumina surface,” Synlett, no. 8, pp. 1275–1278, 2005. View at Publisher · View at Google Scholar · View at Scopus
  65. D. A. Oare and C. H. Heathcock, “Stereochemistry of the base-promoted Michael addition reaction,” in Topics in Stereochemistry, E. L. Eliel and S. H. Willen, Eds., vol. 19, p. 277, John Wiley and Sons, New York, NY, USA, 1989. View at Google Scholar
  66. J. D'Angelo, G. Revial, P. R. R. Costa, R. N. Castro, and O. A. C. Antunes, “Asymmetric Michael addition of chiral imines to phenylvinylsulfone: preparation of key chiral building blocks for the synthesis of Aspidosperma and Hunteria alkaloids,” Tetrahedron Asymmetry, vol. 2, no. 3, pp. 199–202, 1991. View at Publisher · View at Google Scholar · View at Scopus
  67. B. List, P. Pojarliev, and H. J. Martin, “Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins,” Organic Letters, vol. 3, no. 16, pp. 2423–2425, 2001. View at Publisher · View at Google Scholar · View at Scopus
  68. A. Alexakis and O. Andrey, “Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene,” Organic Letters, vol. 4, no. 21, pp. 3611–3614, 2002. View at Publisher · View at Google Scholar · View at Scopus
  69. B. Basu, P. Das, and I. Hossain, “KF-alumina-mediated selective double Michael additions of aryl methyl ketones: a facile entry to the synthesis of functionalized pimelate esters and derivatives,” Synlett, no. 12, pp. 2224–2226, 2004. View at Publisher · View at Google Scholar · View at Scopus
  70. D. A. Horton, G. T. Bourne, and M. L. Smythe, “The combinatorial synthesis of bicyclic privileged structures or privileged substructures,” Chemical Reviews, vol. 103, no. 3, pp. 893–930, 2003. View at Publisher · View at Google Scholar · View at Scopus
  71. G. Bringmann, C. Gunther, M. Ochse, O. Schupp, and S. Tasler, “Biaryls in nature: a multi-facetted class of stereochemically, biosynthetically, and pharmacologically intriguing secondary metabolites,” in Progress in the Chemistry of Organic Natural Products, W. Herz, H. Falk, G. W. Kirby, and R. E. Moore, Eds., vol. 82, Springer, New York, NY, USA, 2001. View at Google Scholar
  72. P. J. Hajduk, M. Bures, J. Praestgaard, and S. W. Fesik, “Privileged molecules for protein binding identified from NMR-based screening,” Journal of Medicinal Chemistry, vol. 43, no. 18, pp. 3443–3447, 2000. View at Publisher · View at Google Scholar · View at Scopus
  73. G. W. Bemis and M. A. Murcko, “The properties of known drugs. 1. Molecular frameworks,” Journal of Medicinal Chemistry, vol. 39, no. 15, pp. 2887–2893, 1996. View at Publisher · View at Google Scholar · View at Scopus
  74. U. Schmidt, V. Leitenberger, H. Griesser, J. Schmidt, and R. Meyer, “Total synthesis of the biphenomycins; V. Synthesis of biphenomycin A,” Synthesis, no. 12, pp. 1248–1254, 1992. View at Google Scholar · View at Scopus
  75. U. Schmidt, R. Meyer, V. Leitenberger, H. Griesser, and A. Lieberknecht, “Total synthesis of the biphenomycins; III. Synthesis of biphenomycin B,” Synthesis, no. 10, pp. 1025–1030, 1992. View at Google Scholar · View at Scopus
  76. A. Markham and K. L. Goa, “Valsartan,” Drugs, vol. 54, no. 2, pp. 299–311, 1997. View at Publisher · View at Google Scholar
  77. K. F. Croom and G. M. Keating, “Valsartan,” American Journal of Cardiovascular Drugs, vol. 4, no. 6, pp. 395–404, 2004. View at Publisher · View at Google Scholar
  78. M. Sharpe, B. Jarvis, and K. L. Goa, “Telmisartan: a review of its use in hypertension,” Drugs, vol. 61, no. 10, pp. 1501–1529, 2001. View at Google Scholar · View at Scopus
  79. S. Yusuf, “From the hope to the ontarget and the transcend studies: challenges in improving prognosis,” American Journal of Cardiology, vol. 89, no. 2, pp. 18–25, 2002. View at Publisher · View at Google Scholar
  80. M. E. Matheron and M. Porchas, “Activity of boscalid, fenhexamid, fluazinam, fludioxonil, and vinclozolin on growth of sclerotinia minor and s. sclerotiorum and development of lettuce drop,” Plant Disease, vol. 88, no. 6, pp. 665–668, 2004. View at Google Scholar · View at Scopus
  81. B. Basu, P. Das, M. M. H. Bhuiyan, and S. Jha, “Microwave-assisted Suzuki coupling on a KF-alumina surface: synthesis of polyaryls,” Tetrahedron Letters, vol. 44, no. 19, pp. 3817–3820, 2003. View at Publisher · View at Google Scholar · View at Scopus
  82. P. Das and B. Basu, “Microwave-assisted copper promoted N-arylation of amines with aryl boronic acids/salts on a KF-alumina surface,” Synthetic Communications, vol. 34, no. 12, pp. 2177–2184, 2004. View at Publisher · View at Google Scholar
  83. A. Gomtsyan, E. K. Bayburt, R. G. Schmidt et al., “Novel transient receptor potential vanilloid 1 receptor antagonists for the treatment of pain; Structure-activity relationships for ureas with quinoline, isoquinoline, quinazoline, phthalazine, quinoxaliue, and cinnoline moieties,” Journal of Medicinal Chemistry, vol. 48, no. 3, pp. 744–752, 2005. View at Publisher · View at Google Scholar · View at Scopus
  84. R. Sarges, H. R. Howard, R. G. Browne, L. A. Lebel, P. A. Seymour, and B. K. Koe, “4-amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants,” Journal of Medicinal Chemistry, vol. 33, no. 8, pp. 2240–2254, 1990. View at Publisher · View at Google Scholar · View at Scopus
  85. L. E. Seitz, W. J. Suling, and R. C. Reynolds, “Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives,” Journal of Medicinal Chemistry, vol. 45, no. 25, pp. 5604–5606, 2002. View at Publisher · View at Google Scholar · View at Scopus
  86. A. Jaso, B. Zarranz, I. Aldana, and A. Monge, “Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti-mycobacterium tuberculosis agents,” Journal of Medicinal Chemistry, vol. 48, no. 6, pp. 2019–2025, 2005. View at Publisher · View at Google Scholar · View at Scopus
  87. W. He, M. R. Myers, B. Hanney et al., “Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity—part 2: the synthesis and biological activities of RPR127963 an orally bioavailable inhibitor,” Bioorganic and Medicinal Chemistry Letters, vol. 13, no. 18, pp. 3097–3100, 2003. View at Publisher · View at Google Scholar · View at Scopus
  88. M. M. Ali, M. M. F. Ismail, M. S. A. El-Gaby, M. A. Zahran, and Y. A. Ammar, “Synthesis and antimicrobial activities of some novel quinoxalinone derivatives,” Molecules, vol. 5, no. 6, pp. 864–873, 2000. View at Google Scholar · View at Scopus
  89. G. Saka, K. Makino, and Y. Kurasawa, “Recent progress in the quinoxaline chemistry. Synthesis and biological activity,” Heterocycles, vol. 27, no. 10, pp. 2481–2515, 1988. View at Google Scholar · View at Scopus
  90. S. Paul and B. Basu, “Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation-condensation or condensation reactions,” Tetrahedron Letters, vol. 52, no. 49, pp. 6597–6602, 2011. View at Publisher · View at Google Scholar · View at Scopus
  91. A. I. Vogel, A. R. Tatchell, B. S. Furnis, A. J. Hannaford, and P. W. G. Smith, Vogel's Textbook of Practical Organic Chemistry, Longman Group, London, UK, 1989.
  92. J. Frackenpohl, P. I. Arvidsson, J. V. Schreiber, and D. Seebach, “The outstanding biological stability of β- and γ-peptides toward proteolytic enzymes: an in vitro investigation with fifteen peptidases,” ChemBioChem, vol. 2, no. 6, pp. 445–455, 2001. View at Google Scholar · View at Scopus
  93. G. Cardillo and C. Tomasini, “Asymmetric synthesis of ß-amino acids and α-substituted β-amino acids,” Chemical Society Reviews, vol. 25, no. 2, pp. 117–128, 1996. View at Publisher · View at Google Scholar
  94. K. C. Nicolaou, V.-M. Dai, and R. K. Guy, “Chemistry and biology of taxol,” Angewandte Chemie—International Edition, vol. 33, no. 1, pp. 15–44, 1994. View at Publisher · View at Google Scholar
  95. F. Texier-Boullet, R. Latouche, and J. Hamelin, “Synthesis in dry media coupled with microwave irradiation: application to the preparation of β-aminoesters and β-lactams via silyl ketene acetals and aldimines,” Tetrahedron Letters, vol. 34, no. 13, pp. 2123–2126, 1993. View at Publisher · View at Google Scholar · View at Scopus
  96. E. J. Corey, C. P. Decicco, and R. C. Newbold, “Highly enantioselective and diastereoselective synthesis of β-amino acid esters and β-lactams from achiral esters and imines,” Tetrahedron Letters, vol. 32, no. 39, pp. 5287–5290, 1991. View at Publisher · View at Google Scholar · View at Scopus
  97. T. N. Salzman, R. W. Ratcliffe, B. G. Christensen, and F. A. Boufford, “A stereocontrolled synthesis of (+)-thienamycin,” Journal of the American Chemical Society, vol. 102, no. 19, pp. 6161–6163, 1980. View at Publisher · View at Google Scholar
  98. J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley and Sons, New York, NY, USA, 1995.
  99. B. Basu, P. Das, and I. Hossain, “Synthesis of β-amino esters via aza-Michael addition of amines to alkenes promoted on silica: a useful and recyclable surface,” Synlett, no. 14, pp. 2630–2632, 2004. View at Publisher · View at Google Scholar · View at Scopus
  100. B. C. Ranu, S. S. Dey, and A. Hajra, “Solvent-free, catalyst-free Michael-type addition of amines to electron-deficient alkenes,” Arkivoc, vol. 2002, no. 7, pp. 76–81, 2002. View at Google Scholar · View at Scopus
  101. C. Brielles, J. J. Harnett, and E. Doris, “Diethylzinc/CuII-mediated alkylation of aromatic amines and related compounds,” Tetrahedron Letters, vol. 42, no. 47, pp. 8301–8302, 2001. View at Publisher · View at Google Scholar · View at Scopus
  102. D. H. R. Barton and E. Doris, “Alkylation of aromatic amines and related compounds using a copper(II)-aluminum(III) couple,” Tetrahedron Letters, vol. 37, no. 19, pp. 3295–3298, 1996. View at Publisher · View at Google Scholar · View at Scopus
  103. S. Yuvaraj, V. V. Balasubramanian, and M. Palanichamy, “N-ethylation of aniline with ethanol or diethyl carbonate over alkali and alkaline zeolites Y and β,” Applied Catalysis A, vol. 176, no. 1, pp. 111–117, 1999. View at Google Scholar · View at Scopus
  104. D. Y. Yoshida and Y. Tanabe, “Direct and selective N-monoalkynylation and N-monoalkenylation of anilines with alky(e)nyl methanesulfonates using methylmagnesium bromide as a base,” Synthesis, no. 5, pp. 533–535, 1997. View at Google Scholar
  105. S. Narayanan and K. Deshpande, “A comparative aniline alkylation activity of montmorillonite and vanadia-montmorillonite with silica and vanadia-silica,” Applied Catalysis A, vol. 135, no. 1, pp. 125–135, 1996. View at Publisher · View at Google Scholar
  106. P. S. Singh, R. Bandyopadhyay, and B. S. Rao, “Aniline methylation over AEL type molecular sieves,” Applied Catalysis A, vol. 136, no. 2, pp. 177–189, 1996. View at Publisher · View at Google Scholar
  107. M. A. Aramendia, V. Borau, C. Jimenez, J. M. Marinas, and F. J. Romero, “N-alkylation of aniline with methanol over magnesium phosphates,” Applied Catalysis A, vol. 183, no. 1, pp. 73–80, 1999. View at Publisher · View at Google Scholar
  108. B. L. Su and D. Barthbomeuf, “Alkylation of aniline with methanol: change in selectivity with acido-basicity of faujasite catalysts,” Applied Catalysis A, vol. 124, no. 1, pp. 73–80, 1995. View at Publisher · View at Google Scholar
  109. I. I. Ivanova, E. B. Pomakhina, A. I. Rebrov, M. Hunger, Y. G. Kolyagin, and J. Weitkamp, “Surface species formed during aniline methylation on zeolite H-Y investigated by in situ MAS NMR spectroscopy,” Journal of Catalysis, vol. 203, no. 2, pp. 375–381, 2001. View at Publisher · View at Google Scholar · View at Scopus
  110. K. Nishamol, K. S. Rahna, and S. Sugunan, “Selective alkylation of aniline to N-methyl aniline using chromium manganese ferrospinels,” Journal of Molecular Catalysis A, vol. 209, no. 1-2, pp. 89–96, 2004. View at Publisher · View at Google Scholar · View at Scopus
  111. K. Okano, H. Tokuyamaand, and T. Fukuyama, “Synthesis of secondary arylamines through copper-mediated intermolecular aryl amination,” Organic Letters, vol. 5, no. 26, pp. 4987–4990, 2003. View at Publisher · View at Google Scholar
  112. A.-N. Ko, C.-L. Yang, W. Zhu, and H. Lin, “Selective N-alkylation of aniline with methanol over γ-alumina,” Applied Catalysis A, vol. 134, no. 1, pp. 53–66, 1996. View at Publisher · View at Google Scholar
  113. M. Selva, P. Tundo, and A. Perosa, “Reaction of primary aromatic amines with alkyl carbonates over NaY faujasite: a convenient and selective access to mono-N-alkyl anilines,” Journal of Organic Chemistry, vol. 66, no. 3, pp. 677–680, 2001. View at Publisher · View at Google Scholar · View at Scopus
  114. B. Basu, S. Paul, and A. K. Nanda, “Highly selective N-alkylation of amines promoted on silica: an efficient and recyclable surface,” Green Chemistry, vol. 11, no. 8, pp. 1115–1120, 2009. View at Publisher · View at Google Scholar · View at Scopus
  115. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, John Wiley and Sons, New York, NY, USA, 1999.
  116. B. J. R. Hanson, Protective Groups in Organic Synthesis, Blackwell Science Inc., Malden, Mass, USA, 1999.
  117. P. A. Hemsley, “Reviews on protein acylation and microdomains in membrane function. Protein S-acylation in plants (review),” Molecular Membrane Biology, vol. 26, pp. 114–125, 2009. View at Publisher · View at Google Scholar
  118. M. F. G. Schmidt, “Fatty acylation of proteins,” Biochimica et Biophysica Acta, vol. 988, no. 3, pp. 411–426, 1989. View at Publisher · View at Google Scholar
  119. R. Leventis, G. Juel, J. K. Knudsen, and J. R. Silvius, “Acyl-CoA binding proteins inhibit the nonenzymic S-acylation of cysteinyl-containing peptide sequences by long-chain acyl-CoAs,” Biochemistry, vol. 36, no. 18, pp. 5546–5553, 1997. View at Publisher · View at Google Scholar · View at Scopus
  120. M. Veit, E. Ponimaskin, and M. F. G. Schmidt, “Analysis of s-acylation of proteins,” Methods in Molecular Biology, vol. 446, pp. 163–182, 2008. View at Publisher · View at Google Scholar · View at Scopus
  121. H. Schroeder, R. Leventis, S. Rex et al., “S-acylation and plasma membrane targeting of the farnesylated carboxyl- terminal peptide of N-ras in mammalian fibroblasts,” Biochemistry, vol. 36, no. 42, pp. 13102–13109, 1997. View at Publisher · View at Google Scholar · View at Scopus
  122. F. Eisele, D. J. Owen, and H. Waldman, “Peptide conjugates as tools for the study of biological signal transduction,” Bioorganic & Medicinal Chemistry, vol. 7, no. 2, pp. 193–224, 1999. View at Publisher · View at Google Scholar
  123. B. Basu, S. Paul, and A. K. Nanda, “Silica-promoted facile synthesis of thioesters and thioethers: a highly efficient, reusable and environmentally safe solid support,” Green Chemistry, vol. 12, no. 5, pp. 767–771, 2010. View at Publisher · View at Google Scholar · View at Scopus
  124. K.-J. Soderlind, B. Gorodetsky, A. K. Singh, N. R. Bachur, G. G. Miller, and J. W. Lown, “Bis-benzimidazole anticancer agents: targeting human tumour helicases,” Anti-Cancer Drug Design, vol. 14, no. 1, pp. 19–36, 1999. View at Google Scholar · View at Scopus
  125. Y. Bai, J. Lu, Z. Shi, and B. Yang, “Synthesis of 2,15-hexadecanedione as a precursor of muscone,” Synlett, no. 4, pp. 544–546, 2001. View at Google Scholar · View at Scopus
  126. E. Bouwman, W. L. Driessen, and J. Reedjik, “Model systems for type I copper proteins: structures of copper coordination compounds with thioether and azole-containing ligands,” Coordination Chemistry Reviews, vol. 104, no. 1, pp. 143–172, 1990. View at Publisher · View at Google Scholar
  127. M. A. Pujar, T. D. Bharamgoudar, and D. N. Sathyanarayana, “Cobalt(II), nickel(II) and copper(II) complexes of bidentate bibenzimidazoles,” Transition Metal Chemistry, vol. 13, no. 6, pp. 423–425, 1988. View at Publisher · View at Google Scholar · View at Scopus
  128. D. Yang, D. Fokas, J. Li, L. Yu, and C. M. Baldino, “A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization,” Synthesis, no. 1, pp. 47–56, 2005. View at Publisher · View at Google Scholar · View at Scopus
  129. R. Trivedi, S. K. De, and R. A. Gibbs, “A convenient one-pot synthesis of 2-substituted benzimidazoles,” Journal of Molecular Catalysis A, vol. 245, no. 1-2, pp. 8–11, 2006. View at Publisher · View at Google Scholar
  130. K. Bahrami, M. M. Khodaei, and I. Kavianinia, “A simple and efficient one-pot synthesis of 2-substituted benzimidazoles,” Synthesis, no. 4, pp. 547–550, 2007. View at Publisher · View at Google Scholar · View at Scopus
  131. K. Bahrami, M. Mehdi Khodaei, and F. Naali, “Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles,” Journal of Organic Chemistry, vol. 73, no. 17, pp. 6835–6837, 2008. View at Publisher · View at Google Scholar · View at Scopus
  132. H. Sharghi, M. Aberi, and M. M. Doroodmand, “Reusable cobalt(III)-salen complex supported on activated carbon as an efficient heterogeneous catalyst for synthesis of 2-arylbenzimidazole derivatives,” Advanced Synthesis and Catalysis, vol. 350, no. 14-15, pp. 2380–2390, 2008. View at Publisher · View at Google Scholar · View at Scopus
  133. Y. X. Chen, L. F. Qian, W. Zhang, and B. Han, “Efficient aerobic oxidative synthesis of 2-substituted benzoxazoles, benzothiazoles, and benzimidazoles catalyzed by 4-methoxy-TEMPO,” Angewandte Chemie—International Edition, vol. 47, no. 48, pp. 9330–9333, 2008. View at Publisher · View at Google Scholar
  134. D. Saha, A. Saha, and B. C. Ranu, “Remarkable influence of substituent in ionic liquid in control of reaction: simple, efficient and hazardous organic solvent free procedure for the synthesis of 2-aryl benzimidazoles promoted by ionic liquid, [pmim]BF4,” Green Chemistry, vol. 11, no. 5, pp. 733–737, 2009. View at Publisher · View at Google Scholar · View at Scopus
  135. C. R. C. Luisa, E. Fernandes, and M. M. B. Marques, “Developments towards regioselective synthesis of 1,2-disubstituted benzimidazoles,” Chemistry—A European Journal, vol. 17, no. 45, pp. 12544–12555, 2011. View at Publisher · View at Google Scholar
  136. S. das Sharma and D. Konwar, “Practical, ecofriendly, and chemoselective method for the synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using amberlite IR-120 as a reusable heterogeneous catalyst in aqueous media,” Synthetic Communications, vol. 39, no. 6, pp. 980–991, 2009. View at Google Scholar
  137. K. Bahrami, M. M. Khodaei, and A. Nejati, “Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles,” Green Chemistry, vol. 12, no. 7, pp. 1237–1241, 2010. View at Publisher · View at Google Scholar · View at Scopus
  138. J.-P. Wan, S.-F. Gan, J.-M. Wu, and Y. Pan, “Water mediated chemoselective synthesis of 1,2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines,” Green Chemistry, vol. 11, no. 10, pp. 1633–1637, 2009. View at Publisher · View at Google Scholar
  139. S. Das Sharma and D. Konwar, Synthetic Communications, vol. 39, no. 6, pp. 980–991, 2009.
  140. S. Santra, A. Majee, and A. Hajra, “Nano indium oxide: an efficient catalyst for the synthesis of 1,2-disubstituted benzimidazoles in aqueous media,” Tetrahedron Letters, vol. 53, no. 15, pp. 1974–1977, 2012. View at Publisher · View at Google Scholar
  141. S. Paul and B. Basu, “Highly selective synthesis of libraries of 1,2-disubstituted benzimidazoles using silica gel soaked with ferric sulfate,” Tetrahedron Letters, vol. 53, no. 32, pp. 4130–4133, 2012. View at Publisher · View at Google Scholar
  142. P. Morys and T. Schlieper, “Synthesis and catalytic activity of silica supported iron(III),” Journal of Molecular Catalysis A, vol. 95, no. 1, pp. 27–33, 1995. View at Publisher · View at Google Scholar
  143. J. Xu and C. H. Bartholomew, “Temperature-programmed hydrogenation (TPH) and in situ Mössbauer spectroscopy studies of carbonaceous species on silica-supported iron Fischer-Tropsch catalysts,” The Journal of Physical Chemistry B, vol. 109, no. 6, pp. 2392–2403, 2005. View at Publisher · View at Google Scholar
  144. D. D. E. Koyuncu and S. Yasyerli, “Selectivity and stability enhancement of iron oxide catalyst by Ceria Incorporation for selective oxidation of H2S to sulfur,” Industrial & Engineering Chemistry Research, vol. 48, no. 11, pp. 5223–5229, 2009. View at Publisher · View at Google Scholar
  145. D. J. Kim, B. C. Dunn, F. Huggins et al., “SBA-15-supported iron catalysts for Fischer-Tropsch production of diesel fuel,” Energy and Fuels, vol. 20, no. 6, pp. 2608–2611, 2006. View at Publisher · View at Google Scholar · View at Scopus
  146. G. A. Bukhtiyarova, V. I. Bukhtiyarov, N. S. Sakaeva, V. V. Kaichev, and B. P. Zolotovskii, “XPS study of the silica-supported Fe-containing catalysts for deep or partial H2S oxidation,” Journal of Molecular Catalysis A, vol. 158, no. 1, pp. 251–255, 2000. View at Publisher · View at Google Scholar · View at Scopus
  147. Z. Ma, Y. Ke, H. Wang et al., “Ethylene polymerization with a silica-supported iron-based diimine catalyst,” Journal of Applied Polymer Science, vol. 88, no. 2, pp. 466–469, 2003. View at Publisher · View at Google Scholar
  148. A.-T. Pham, C. Lee, F. M. Doyle, and D. L. Sedlak, “A silica-supported iron oxide catalyst capable of activating hydrogen peroxide at neutral pH values,” Environmental Science & Technology, vol. 43, no. 23, pp. 8930–8935, 2009. View at Publisher · View at Google Scholar
  149. S. Moreton, “Silica gel impregnated with iron(III) salts: a safe humidity indicator,” Material Research Innovations, vol. 5, no. 5, pp. 226–229, 2002. View at Publisher · View at Google Scholar
  150. K. Bahrami, M. M. Khodaei, and A. Nejati, “Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles,” Green Chemistry, vol. 12, no. 7, pp. 1237–1241, 2010. View at Publisher · View at Google Scholar · View at Scopus
  151. M. Amirnasr, K. J. Schenk, A. Gorji, and R. Vafazadeh, “Synthesis and spectroscopic characterization of [CoIII(salophen)(amine)2]ClO4 (amine = morpholine, pyrrolidine, and piperidine) complexes. The crystal structures of [CoIII(salophen)(morpholine)2]ClO4 and [CoIII(salophen)(pyrrolidine)2]ClO4,” Polyhedron, vol. 20, no. 7-8, pp. 695–702, 2001. View at Publisher · View at Google Scholar · View at Scopus
  152. K. W. Pepper, H. M. Paisley, and M. A. Young, “Properties of ion-exchange resins in relation to their structure—part VI: anion-exchange resins derived from styrene-divinyl-benzene copolymers,” Journal of the Chemical Society, pp. 4097–4105, 1953. View at Publisher · View at Google Scholar
  153. R. V. Law, D. C. Sherrington, C. E. Snape, I. Ando, and H. Kurosu, “Solid-state13C MAS NMR studies of hyper-cross-linked polystyrene resins,” Macromolecules, vol. 29, no. 19, pp. 6284–6293, 1996. View at Google Scholar · View at Scopus
  154. S. Pickup, F. D. Blum, W. T. Ford, and M. Periyasamy, “Transport of small molecules in swollen polymer beads,” Journal of the American Chemical Society, vol. 108, no. 14, pp. 3987–3990, 1986. View at Google Scholar · View at Scopus
  155. T. Balakrishnan and W. T. Ford, “Particle size control in suspension copolymerization of styrene, chloromethylstyrene, and divinylbenzene,” Journal of Applied Polymer Science, vol. 27, no. 1, pp. 133–138, 1982. View at Publisher · View at Google Scholar
  156. R. Quarrell, T. D. Claridge, G. W. Weaver, and G. Lowe, “Structure and properties of TentaGel resin beads: implications for combinatorial library chemistry,” Molecular Diversity, vol. 4, no. 4, pp. 223–232, 1996. View at Publisher · View at Google Scholar
  157. C. M. G. Judkins, K. A. Knights, B. F. G. Johnson, Y. R. de Miguel, R. Raja, and J. M. Thomas, “Immobilisation of ruthenium cluster catalysts via novel derivatisations of ArgoGel resins,” Chemical Communications, no. 24, pp. 2624–2625, 2001. View at Google Scholar · View at Scopus
  158. D. Astruc, Nanoparticles and Catalysis, Wiley-VCH, Weinheim, Germany, 2008.
  159. S. Kobayashi and R. Akiyama, “Renaissance of immobilized catalysts. New types of polymer-supported catalysts, ‘microencapsulated catalysts’, which enable environmentally benign and powerful high-throughput organic synthesis,” Chemical Communications, no. 4, pp. 449–460, 2003. View at Publisher · View at Google Scholar
  160. S. Kobayashi and R. Akiyama, “New methods for high-throughput synthesis,” Pure and Applied Chemistry, vol. 73, no. 7, pp. 1103–1111, 2001. View at Google Scholar · View at Scopus
  161. P. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, New York, NY, USA, 1979.
  162. N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, NY, USA, 2001.
  163. E. A. Braude and R. P. Linstead, “Hydrogen transfer—part I: introductory survey,” Journal of the Chemical Society, pp. 3544–3547, 1954. View at Publisher · View at Google Scholar · View at Scopus
  164. G. Brieger and T. J. Nestrick, “Catalytic transfer hydrogenation,” Chemical Reviews, vol. 74, no. 5, pp. 567–580, 1974. View at Google Scholar · View at Scopus
  165. R. A. W. Johnstone, A. H. Wilby, and I. D. Entwistle, “Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds,” Chemical Reviews, vol. 85, no. 2, pp. 129–170, 1985. View at Google Scholar · View at Scopus
  166. M. Takasaki, Y. Motoyama, K. Higashi, S.-H. Yoon, I. Mochida, and H. Nagashima, “Chemoselective hydrogenation of nitroarenes with carbon nanofiber-supported platinum and palladium nanopraticles,” Organic Letters, vol. 10, no. 8, pp. 1601–1604, 2008. View at Publisher · View at Google Scholar · View at Scopus
  167. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, and P. Selvam, “Heterogeneous catalytic transfer hydrogenation of aromatic nitro and carbonyl compounds over cobalt(II) substituted hexagonal mesoporous aluminophosphate molecular sieves,” Tetrahedron Letters, vol. 43, no. 47, pp. 8527–8529, 2002. View at Publisher · View at Google Scholar · View at Scopus
  168. R. V. Jagadeesh, G. Wienhöfer, F. A. Westerhaus et al., “Efficient and highly selective iron-catalyzed reduction of nitroarenes,” Chemical Communications, vol. 47, no. 39, pp. 10972–10974, 2011. View at Publisher · View at Google Scholar · View at Scopus
  169. A. Saha and B. C. Ranu, “Highly chemoselective reduction of aromatic nitro compounds by copper nanoparticles/ammonium formate,” The Journal of Organic Chemistry, vol. 73, no. 17, pp. 6867–6870, 2008. View at Publisher · View at Google Scholar · View at Scopus
  170. R. J. Rahaim Jr. and R. E. Maleczka Jr., “Pd-catalyzed silicon hydride reductions of aromatic and aliphatic nitro groups,” Organic Letters, vol. 7, no. 22, pp. 5087–5090, 2005. View at Publisher · View at Google Scholar · View at Scopus
  171. K. Nomura, “Efficient selective reduction of aromatic nitro compounds by ruthenium catalysis under CO/H2O conditions,” Journal of Molecular Catalysis A, vol. 95, no. 3, pp. 203–210, 1995. View at Publisher · View at Google Scholar
  172. L. He, L.-C. Wang, H. Sun et al., “Efficient and selective room-temperature gold-catalyzed reduction of nitro compounds with CO and H2O as the hydrogen source,” Angewandte Chemie—International Edition, vol. 48, no. 50, pp. 9538–9541, 2009. View at Publisher · View at Google Scholar
  173. R. V. Niquirilo, E. Teixeira-Neto, G. S. Buzzo, and H. B. Suffredini, “Formic acid oxidation at Pd, Pt and PbOx-based catalysts and calculation of their approximate electrochemical active areas,” International Journal of Electrochemical Science, vol. 5, no. 3, pp. 344–354, 2010. View at Google Scholar · View at Scopus
  174. B. Basu, M. M. H. Bhuiyan, P. Das, and I. Hossain, “Catalytic transfer reduction of conjugated alkenes and an imine using polymer-supported formates,” Tetrahedron Letters, vol. 44, no. 50, pp. 8931–8934, 2003. View at Publisher · View at Google Scholar · View at Scopus
  175. N. A. Cortese and R. F. Heck, “Palladium catalyzed reductions of halo- and nitroaromatic compounds with triethylammonium formate,” The Journal of Organic Chemistry, vol. 42, no. 22, pp. 3491–3494, 1977. View at Publisher · View at Google Scholar
  176. H. Weiner, J. Blum, and Y. Sasson, “Studies on the mechanism of transfer hydrogenation of nitro arenes by formate salts catalyzed by palladium/carbon,” The Journal of Organic Chemistry, vol. 56, no. 14, pp. 4481–4486, 1991. View at Publisher · View at Google Scholar
  177. D. C. Gowda, A. S. P. Gowda, A. R. Baba, and S. Gowda, “Nickel-catalyzed formic acid reductions. A selective method for the reduction of nitro compounds,” Synthetic Communications, vol. 30, no. 16, pp. 2889–2895, 2000. View at Google Scholar · View at Scopus
  178. K. Hanaya, T. Muramatsu, H. Kudo, and Y. L. Chow, “Reduction of aromatic nitro-compounds to amines with sodium borohydride-copper(II) acetylacetonate,” Journal of the Chemical Society, Perkin Transactions 1, pp. 2409–2410, 1979. View at Google Scholar · View at Scopus
  179. N. Pradhan, A. Pal, and T. Pal, “Silver nanoparticle catalyzed reduction of aromatic nitro compounds,” Colloids and Surfaces A, vol. 196, no. 2-3, pp. 247–257, 2002. View at Publisher · View at Google Scholar · View at Scopus
  180. B. Basu, P. Das, and S. Das, “Transfer hydrogenation using recyclable polymer-supported formate (PSF): efficient and chemoselective reduction of nitroarenes,” Molecular Diversity, vol. 9, no. 4, pp. 259–262, 2005. View at Publisher · View at Google Scholar
  181. P. Selvam, S. K. Mohapatra, S. U. Sonavane, and R. V. Jayaram, “Chemo- and regioselective reduction of nitroarenes, carbonyls and azo dyes over nickel-incorporated hexagonal mesoporous aluminophosphate molecular sieves,” Tetrahedron Letters, vol. 45, no. 9, pp. 2003–2007, 2004. View at Publisher · View at Google Scholar · View at Scopus
  182. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, and P. Selvam, “Reductive cleavage of azo dyes and reduction of nitroarenes over trivalent iron incorporated hexagonal mesoporous aluminophosphate molecular sieves,” Applied Catalysis B, vol. 46, no. 1, pp. 155–163, 2003. View at Publisher · View at Google Scholar · View at Scopus
  183. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, and P. Selvam, “Heterogeneous catalytic transfer hydrogenation of aromatic nitro and carbonyl compounds over cobalt(II) substituted hexagonal mesoporous aluminophosphate molecular sieves,” Tetrahedron Letters, vol. 43, no. 47, pp. 8527–8529, 2002. View at Publisher · View at Google Scholar · View at Scopus
  184. S. K. Mohapatra, S. U. Sonavane, R. V. Jayaram, and P. Selvam, “Regio- and chemoselective catalytic transfer hydrogenation of aromatic nitro and carbonyl as well as reductive cleavage of azo compounds over novel mesoporous NiMCM-41 molecular sieves,” Organic Letters, vol. 4, no. 24, pp. 4297–4300, 2002. View at Publisher · View at Google Scholar
  185. A. S. Kulkarni and R. V. Jayaram, “Liquid phase catalytic transfer hydrogenation of aromatic nitro compounds on perovskites prepared by microwave irradiation,” Applied Catalysis A, vol. 252, no. 2, pp. 225–230, 2003. View at Publisher · View at Google Scholar
  186. A. S. Kulkarni and R. V. Jayaram, “Liquid phase catalytic transfer hydrogenation of aromatic nitro compounds on La1−xSrxFeO3 perovskites prepared by microwave irradiation,” Journal of Molecular Catalysis A, vol. 223, pp. 107–110, 2004. View at Publisher · View at Google Scholar
  187. B. Basu, B. Mandal, S. Das, P. Das, and A. K. Nanda, “Chemoselective reduction of aldehydes by ruthenium trichloride and resin-bound formates,” The Beilstein Journal of Organic Chemistry, vol. 4, no. 53, 2008. View at Publisher · View at Google Scholar
  188. B. Basu, S. Das, P. Das, and A. K. Nanda, “Co-immobilized formate anion and palladium on a polymer surface: a novel heterogeneous combination for transfer hydrogenation,” Tetrahedron Letters, vol. 46, no. 49, pp. 8591–8593, 2005. View at Publisher · View at Google Scholar · View at Scopus
  189. E.-I. Negishi, Organopalladium Chemistry for Organic Synthesis, Wiley-InterScience, New York, NY, USA, 2002.
  190. A. D. Meijere and F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 2004.
  191. C. C. Mauger and G. A. Mignani, “Synthetic applications of Buchwald's phosphines in palladium-catalyzed aromatic-bond-forming reactions,” Aldrichimica Acta, vol. 39, no. 1, pp. 17–24, 2006. View at Google Scholar · View at Scopus
  192. W. A. Herrmann, K. Öfele, D. V. Preysing, and S. K. Schneider, “Phospha-palladacycles and N-heterocyclic carbene palladium complexes: efficient catalysts for CC-coupling reactions,” Journal of Organometallic Chemistry, vol. 687, no. 2, pp. 229–248, 2003. View at Publisher · View at Google Scholar
  193. L. Yin and J. Liebscher, “Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts,” Chemical Reviews, vol. 107, no. 1, pp. 133–173, 2007. View at Publisher · View at Google Scholar
  194. K. Sonogashira, Y. Tohda, and N. Hagihara, “A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines,” Tetrahedron Letters, vol. 16, no. 50, pp. 4467–4470, 1975. View at Google Scholar · View at Scopus
  195. K. Sonogashira, “Coupling reactions between sp2 and sp carbon centers,” in Comprehensive Organic Synthesis, B. M. Trost, Ed., vol. 3, pp. 521–549, Pergamon Press, Oxford, UK, 1999. View at Google Scholar
  196. C. J. S. Wu, M. D. Watson, L. Zhang, Z. H. Wang, and K. Mullen, “Hexakis(4-iodophenyl)-peri-hexabenzocoronene—a versatile building block for highly ordered discotic liquid crystalline materials,” Journal of the American Chemical Society, vol. 126, no. 1, pp. 177–186, 2004. View at Publisher · View at Google Scholar
  197. G. Hennrich and A. M. Echavarren, “New persubstituted 1,3,5-trisethynyl benzenes via Sonogashira coupling,” Tetrahedron Letters, vol. 45, no. 6, pp. 1147–1149, 2004. View at Publisher · View at Google Scholar · View at Scopus
  198. J. N. Wilson, M. Josowicz, Y. Q. Wang, and U. H. F. Bunz, “Cruciform π-systems: hybrid phenylene-ethynylene/phenylene-vinylene oligomers,” Chemical Communications, no. 24, pp. 2962–2963, 2003. View at Publisher · View at Google Scholar
  199. C. C. Li, Z. X. Xie, Y. D. Zhang, J. H. Chen, and Z. Yang, “Total synthesis of wedelolactone,” The Journal of Organic Chemistry, vol. 68, no. 22, pp. 8500–8504, 2003. View at Publisher · View at Google Scholar
  200. K. Y. Tsang, M. A. Brimble, and J. B. Bremner, “Use of a sonogashira-acetylide coupling strategy for the synthesis of the aromatic spiroketal skeleton of γ-rubromycin,” Organic Letters, vol. 5, no. 23, pp. 4425–4427, 2003. View at Publisher · View at Google Scholar · View at Scopus
  201. I. Paterson, R. D. M. Davies, A. L. Heimann, R. Maquez, and A. Meyer, “Stereocontrolled total synthesis of (−)-callipeltoside A,” Organic Letters, vol. 5, no. 23, pp. 4477–4480, 2003. View at Publisher · View at Google Scholar
  202. J. W. Lane and R. L. Halcomb, “A new method for the stereoselective synthesis of α-substituted serine amino acid analogues,” Organic Letters, vol. 5, no. 22, pp. 4017–4020, 2003. View at Publisher · View at Google Scholar
  203. T. M. Hansen, M. M. Engler, and C. J. Forsyth, “Total synthesis of a biotinylated derivative of phorboxazole A via sonogashira coupling,” Bioorganic & Medicinal Chemistry Letters, vol. 13, no. 13, pp. 2127–2130, 2003. View at Google Scholar
  204. N. Ohyaba, T. Nishkawa, and M. Isobe, “First asymmetric total synthesis of tetrodotoxin,” Journal of the American Chemical Society, vol. 125, no. 29, pp. 8798–8805, 2003. View at Publisher · View at Google Scholar
  205. J. A. Marshall and G. M. Schaaf, “Total synthesis and structure confirmation of leptofuranin D,” Journal of Organic Chemistry, vol. 68, no. 19, pp. 7428–7432, 2003. View at Google Scholar · View at Scopus
  206. S. Lopez, F. Fernandeztrillo, L. Castedo, and C. Saa, “Synthesis of callyberynes A and B, polyacetylenic hydrocarbons from marine sponges,” Organic Letters, vol. 5, no. 20, pp. 3275–3728, 2003. View at Publisher · View at Google Scholar
  207. D. W. C. MacMillan, “The advent and development of organocatalysis,” Nature, vol. 455, no. 7211, pp. 304–308, 2008. View at Publisher · View at Google Scholar · View at Scopus
  208. S. Kobayashi and K. Manabe, “Development of novel Lewis acid catalysts for selective organic reactions in aqueous media,” Accounts of Chemical Research, vol. 35, no. 4, pp. 209–217, 2002. View at Publisher · View at Google Scholar
  209. H. C. Kolb, M. G. Finn, and K. B. Sharpless, “Click chemistry: diverse chemical function from a few good reactions,” Angewandte Chemie—International Edition, vol. 40, no. 11, pp. 2004–2021, 2001. View at Google Scholar
  210. S. R. Chemler, D. Trauner, and S. J. Danishefsky, “The b-alkyl Suzuki-Miyaura cross-coupling reaction: development, mechanistic study, and applications in natural product synthesis,” Angewandte Chemie—International Edition, vol. 40, no. 24, pp. 4544–4568, 2001. View at Google Scholar
  211. N. Miyaura, “Synthesis of biaryls via the cross-coupling reaction of arylboronic acids,” Advances in Metal-Organic Chemistry, vol. 6, pp. 187–243, 1998. View at Publisher · View at Google Scholar
  212. L. F. Tietze, G. Kettschau, U. Heuschert, and G. Nordman, “Highly efficient synthesis of linear pyrrole oligomers by twofold Heck reactions,” Chemistry—A European Journal, vol. 7, no. 2, pp. 368–373, 2001. View at Google Scholar
  213. S. Kotha, K. Lahiri, and D. Kashinath, “Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis,” Tetrahedron, vol. 58, no. 48, pp. 9633–9695, 2002. View at Publisher · View at Google Scholar · View at Scopus
  214. D. Alberico, M. E. Scott, and M. Lautens, “Aryl-aryl bond formation by transition-metal-catalyzed direct arylation,” Chemical Reviews, vol. 107, no. 1, pp. 174–238, 2007. View at Publisher · View at Google Scholar · View at Scopus
  215. I. P. Beletskaya and A. V. Cheprakov, “Heck reaction as a sharpening stone of palladium catalysis,” Chemical Reviews, vol. 100, no. 8, pp. 3009–3066, 2000. View at Publisher · View at Google Scholar · View at Scopus
  216. K. C. Nicolaou, H. Li, C. N. C. Boddy et al., “Total synthesis of vancomycin—part 1: design and development of methodology,” Chemistry—A European Journal, vol. 5, no. 9, pp. 2584–2601, 1999. View at Google Scholar · View at Scopus
  217. K. Kamikawa, T. Watanabe, A. Daimon, and M. Uemura, “Stereoselective synthesis of axially chiral natural products, (-)-steganone and O,O′-dimethylkorupensamine A, utilizing planar chiral (arene)chromium complexes,” Tetrahedron, vol. 56, no. 15, pp. 2325–2337, 2000. View at Publisher · View at Google Scholar
  218. A. Haberli and C. J. Leumann, “Synthesis of pyrrolidine C-nucleosides via heck reaction,” Organic Letters, vol. 3, no. 3, pp. 489–492, 2001. View at Publisher · View at Google Scholar
  219. http://www.nobelprize.org/.
  220. C. Ramarao, S. V. Ley, S. C. Smith, I. M. Shirley, and N. D. Almerda, “Encapsulation of palladium in polyurea microcapsules,” Chemical Communications, no. 10, pp. 1132–1133, 2002. View at Publisher · View at Google Scholar
  221. J. Q. Yu, H. C. Wu, C. Ramarao, J. B. Spencer, and S. V. Ley, “Transfer hydrogenation using recyclable polyurea-encapsulated palladium: efficient and chemoselective reduction of aryl ketones,” Chemical Communications, no. 6, pp. 678–679, 2003. View at Publisher · View at Google Scholar
  222. S. V. Ley, C. Mitchell, D. Pears, C. Ramarao, J.-Q. Yu, and W. Zhou, “Recyclable polyurea-microencapsulated Pd(0) nanoparticles: an efficient catalyst for hydrogenolysis of epoxides,” Organic Letters, vol. 5, no. 24, pp. 4665–4668, 2003. View at Publisher · View at Google Scholar · View at Scopus
  223. V. Chechik and R. M. Crooks, “Dendrimer-encapsulated Pd nanoparticles as fluorous phase-soluble catalysts,” Journal of the American Chemical Society, vol. 122, no. 6, pp. 1243–1244, 2000. View at Publisher · View at Google Scholar
  224. S. Kobayashi and S. Nagayama, “A microencapsulated Lewis acid: a new type of polymer-supported Lewis acid catalyst of wide utility in organic synthesis,” Journal of the American Chemical Society, vol. 120, no. 12, pp. 2985–2986, 1998. View at Publisher · View at Google Scholar
  225. S. Kobayashi, M. Endo, and S. Nagayama, “Catalytic asymmetric dihydroxylation of olefins using a recoverable and reusable polymer-supported osmium catalyst,” Journal of the American Chemical Society, vol. 121, no. 48, pp. 11229–11230, 1999. View at Publisher · View at Google Scholar · View at Scopus
  226. R. Akiyama and S. Kobayashi, “Microencapsulated palladium catalysts: allylic substitution and Suzuki coupling using a recoverable and reusable polymer-supported palladium catalyst,” Angewandte Chemie—International Edition, vol. 40, no. 18, pp. 3469–3471, 2001. View at Google Scholar
  227. R. Akiyama and S. Kobayashi, “A novel polymer-supported arene-ruthenium complex for ring-closing olefin metathesis,” Angewandte Chemie—International Edition, vol. 41, no. 14, pp. 2602–2604, 2002. View at Google Scholar
  228. R. Akiyama and S. Kobayashi, “The polymer incarcerated method for the preparation of highly active heterogeneous palladium catalysts,” Journal of the American Chemical Society, vol. 125, no. 12, pp. 3412–3413, 2003. View at Publisher · View at Google Scholar
  229. K. Okamota, R. Akiyama, and S. Kobayashi, “Recoverable, reusable, highly active, and sulfur-tolerant polymer incarcerated palladium for hydrogenation,” The Journal of Organic Chemistry, vol. 69, pp. 2871–2873, 2004. View at Publisher · View at Google Scholar
  230. K. Okamota, R. Akiyama, and S. Kobayashi, “Suzuki-Miyaura coupling catalyzed by polymer-incarcerated palladium, a highly active, recoverable, and reusable Pd catalyst,” Organic Letters, vol. 6, no. 12, pp. 1987–1990, 2004. View at Publisher · View at Google Scholar
  231. L. K. Okamota, R. Akiyama, H. Yoshida, T. Yoshida, and S. Kobayashi, “Formation of nanoarchitectures including subnanometer palladium clusters and their use as highly active catalysts,” Journal of the American Chemical Society, vol. 127, no. 7, pp. 2125–2135, 2005. View at Publisher · View at Google Scholar
  232. H. Hagio, M. Sugiura, and S. Kobayashi, “Practical preparation method of polymer-incarcerated (PI) palladium catalysts using Pd(II) salts,” Organic Letters, vol. 8, no. 3, pp. 375–378, 2006. View at Publisher · View at Google Scholar
  233. L. Strimbu, J. Liu, and A. E. Kaifer, “Cyelodextrin-capped palladium nanoparticles as catalysts for the Suzuki reaction,” Langmuir, vol. 19, no. 2, pp. 483–485, 2003. View at Publisher · View at Google Scholar · View at Scopus
  234. E. H. Rahim, F. S. Kamounah, J. Frederiksen, and J. B. Christensen, “Heck reactions catalyzed by PAMAM-dendrimer encapsulated Pd(0) nanoparticles,” Nano Letters, vol. 1, no. 9, pp. 499–501, 2001. View at Publisher · View at Google Scholar · View at Scopus
  235. M. Pittelkow, K. Moth-Poulsen, U. Boas, and J. B. Christensen, “Poly(amidoamine)-dendrimer-stabilized Pd(0) nanoparticles as a catalyst for the Suzuki reaction,” Langmuir, vol. 19, no. 18, pp. 7682–7684, 2003. View at Publisher · View at Google Scholar · View at Scopus
  236. J. C. Garcia-Martinez, R. Lezutekong, and R. M. Crooks, “Dendrimer-encapsulated Pd nanoparticles as aqueous, room-temperature catalysts for the Stille reaction,” Journal of the American Chemical Society, vol. 127, no. 14, pp. 5097–5103, 2005. View at Publisher · View at Google Scholar · View at Scopus
  237. D. Basu, S. Das, P. Das, B. Mandal, D. Banerjee, and F. Almqvist, “Palladium supported on a polyionic resin as an efficient, ligand-free, and recyclable catalyst for Heck, Suzuki-Miyaura, and Sonogashira reactions,” Synthesis, no. 7, pp. 1137–1146, 2009. View at Publisher · View at Google Scholar · View at Scopus
  238. A. Kirschning, H. Monenschein, and R. Wittenberg, “The “resin-capture-release” hybrid technique: a merger between solid- and solution-phase synthesis,” Chemistry—A European Journal, vol. 6, no. 24, pp. 4445–4450, 2000. View at Google Scholar · View at Scopus
  239. http://www.cypress-international.com/image/polymerlabs/pldmap.pdf.
  240. S. Khound and P. J. Das, “Solid phase synthesis of N-arylazoindoles,” Tetrahedron, vol. 53, no. 28, pp. 9749–9754, 1997. View at Publisher · View at Google Scholar · View at Scopus
  241. S. Roller, H. Turk, J.-F. Stumbe, W. Rapp, and R. Haag, “Polystyrene-graft-polyglycerol resins: a new type of high-loading hybrid support for organic synthesis,” Journal of Combinatorial Chemistry, vol. 8, no. 3, pp. 350–354, 2006. View at Publisher · View at Google Scholar
  242. Y. Zheng, P. D. Stevens, and Y. Gao, “Magnetic nanoparticles as an orthogonal support of polymer resins: applications to solid-phase suzuki cross-coupling reactions,” The Journal of Organic Chemistry, vol. 71, no. 2, pp. 537–542, 2006. View at Publisher · View at Google Scholar
  243. T. E. Nielsen, S. Le Quement, and M. Meldal, “Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions,” Tetrahedron Letters, vol. 46, no. 46, pp. 7959–7962, 2005. View at Publisher · View at Google Scholar · View at Scopus
  244. J. F. Brown, P. Krajnc, and N. R. Cameron, “PolyHIPE supports in batch and flow-through suzuki cross-coupling reactions,” Industrial & Engineering Chemistry Research, vol. 44, no. 23, pp. 8565–8572, 2005. View at Publisher · View at Google Scholar
  245. J. T. Bork, J. W. Lee, and Y.-T. Chang, “Palladium-catalyzed cross-coupling reaction of resin-bound chlorotriazines,” Tetrahedron Letters, vol. 44, no. 32, pp. 6141–6144, 2003. View at Publisher · View at Google Scholar · View at Scopus
  246. J. V. Wade and C. A. Krueger, “Suzuki cross-coupling of solid-supported chloropyrimidines with arylboronic acids,” Journal of Combinatorial Chemistry, vol. 5, no. 3, pp. 267–272, 2003. View at Publisher · View at Google Scholar
  247. A. Hebel and R. Haag, “Polyglycerol as a high-loading support for boronic acids with application in solution-phase Suzuki cross-couplings,” Journal of Organic Chemistry, vol. 67, no. 26, pp. 9452–9455, 2002. View at Publisher · View at Google Scholar · View at Scopus
  248. G. Wulff, H. Schmidt, H. Witt, and R. Zentel, “Cooperativity and transfer of chirality in liquid-crystalline polymers,” Angewandte Chemie—International Edition, vol. 33, no. 2, pp. 188–191, 1994. View at Publisher · View at Google Scholar
  249. J. W. Guiles, S. G. Johnson, and W. V. Murray, “Solid-phase Suzuki coupling for C-C bond formation,” Journal of Organic Chemistry, vol. 61, no. 15, pp. 5169–5171, 1996. View at Google Scholar · View at Scopus
  250. S. R. Piettre and S. Baltzer, “A new approach to the solid-phase Suzuki coupling reaction,” Tetrahedron Letters, vol. 38, no. 7, pp. 1197–1200, 1997. View at Publisher · View at Google Scholar · View at Scopus
  251. R. J. Kell, P. Hodge, M. Nisar, and R. T. Williams, “Facile attachment of functional moieties to crosslinked polystyrene beads via robust linkages: Suzuki reactions using polymer-supported boronic acids,” Journal of the Chemical Society. Perkin Transactions 1, no. 24, pp. 3403–3408, 2001. View at Google Scholar · View at Scopus
  252. Y. Han, S. D. Walker, and R. N. Young, “Silicon directed ipso-substitution of polymer bound arylsilanes: preparation of biaryls via the Suzuki cross-coupling reaction,” Tetrahedron Letters, vol. 37, no. 16, pp. 2703–2706, 1996. View at Publisher · View at Google Scholar
  253. V. Lobrégat, G. Alcaraz, H. Bienayme, and M. Vaultier, “Application of the ‘resin-capture-release’ methodology to macrocyclisation via intramolecular Suzuki-Miyaura coupling,” Chemical Communications, no. 9, p. 817, 2001. View at Publisher · View at Google Scholar
  254. M. J. Farrall and J. M. J. Fréchet, “Bromination and lithiation: two important steps in the functionalization of polystyrene resins,” The Journal of Organic Chemistry, vol. 41, no. 24, pp. 3877–3882, 1976. View at Publisher · View at Google Scholar
  255. R. Frenette and R. W. Friesen, “Biaryl synthesis via suzuki coupling on a solid support,” Tetrahedron Letters, vol. 35, no. 49, pp. 9177–9180, 1994. View at Publisher · View at Google Scholar · View at Scopus
  256. B. Basu, S. Das, S. Kundu, and B. Mandal, “Polyionic heterogeneous phenylating agent for base-free Suzuki-Miyaura coupling reaction,” Synlett, no. 2, pp. 255–259, 2008. View at Publisher · View at Google Scholar · View at Scopus
  257. D. C. Jocelyn, Biochemistry of the Thiol Group, Academic Press, New York, NY, USA, 1992.
  258. M. Bodzansky, Principles of Peptide Synthesis, chapter 4, Springer, Berlin, Germany, 1984.
  259. G. Capozzi and G. Modena, “Oxidation of thiol,” in The Chemistry of the Thiol Group, Part II, S. Patai, Ed., p. 785, John Wiley and Sons, New York, NY, USA, 1975. View at Google Scholar
  260. K. Inaba, “Disulfide bond formation system in Escherichia coli,” Journal of Biochemistry, vol. 146, no. 5, pp. 591–597, 2009. View at Publisher · View at Google Scholar · View at Scopus
  261. W. J. Wedemeyer, E. Welker, M. Narayan, and H. A. Scheraga, “Disulfide bonds and protein folding,” Biochemistry, vol. 39, no. 15, pp. 4207–4216, 2000. View at Publisher · View at Google Scholar · View at Scopus
  262. K. Ramadas and N. Srinivasan, “Sodium chlorite—yet another oxidant for thiols to disulphides,” Synthetic Communications, vol. 25, no. 2, pp. 227–234, 1995. View at Publisher · View at Google Scholar
  263. H. L. Fisher, “Elastomers,” Industrial & Engineering Chemistry, vol. 42, no. 10, pp. 1978–1982, 1950. View at Publisher · View at Google Scholar
  264. D. Sengupta and B. Basu, “An efficient metal-free synthesis of organic disulfides from thiocyanates using poly-ionic resin hydroxide in aqueous medium,” Tetrahedron Letters, vol. 54, no. 18, pp. 2277–2281, 2013. View at Publisher · View at Google Scholar