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Journal of Chemistry
Volume 2013, Article ID 268649, 7 pages
http://dx.doi.org/10.1155/2013/268649
Research Article

Rapid Reduction of Alkenes and Alkynes over Pd Nanoparticles Supported on Sulfonated Porous Carbon

Chemistry Department, Malek-Ashtar University of Technology, P.O. Box 83145-115, Shahin Shahr, Iran

Received 5 January 2012; Accepted 6 June 2012

Academic Editor: Matthias D'hooghe

Copyright © 2013 Arash Shokrolahi et al. 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. P. N. Rylander, Hydrogenation Methods, Academic Press, San Diego, Calif, USA, 1994.
  2. M. Hudlicky, Reductions in Organic Chemistry, John Wiley & Sons, New York, NY, USA, 1984.
  3. E. Baralt and N. Holy, “Hydrogenation of nitro compounds with an anthranilic acid polymer-bound catalyst,” Journal of Organic Chemistry, vol. 49, no. 14, pp. 2626–2627, 1984. View at Google Scholar · View at Scopus
  4. H. I. Schlesinger, H. C. Brown, H. R. Hoekstra, and L. R. Rapp, “Reactions of diborane with alkali metal hydrides and their addition compounds. New syntheses of borohydrides. Sodium and potassium borohydrides,” Journal of the American Chemical Society, vol. 75, no. 1, pp. 199–204, 1953. View at Google Scholar · View at Scopus
  5. H. C. Brown and R. B. C. Subba, “Reduction of esters and other di cultly reducible groups by sodium borohydride,” Journal of the American Chemical Society, vol. 77, p. 3164, 1955. View at Google Scholar
  6. H. C. Brown, Boranes in Organic Chemistry, Cornell University Press, Ithaca, NY, 1972.
  7. H. C. Brown and S. Krishnamurthy, “Forty years of hydride reductions,” Tetrahedron, vol. 35, no. 5, pp. 567–607, 1979. View at Google Scholar · View at Scopus
  8. G. W. Gribble and C. F. Nutaitis, “Sodium borohydride in carboxylic acid media. A review of the synthetic utility of acyloxyborohydrides,” Organic Preparations and Procedures International, vol. 17, p. 317, 1985. View at Google Scholar
  9. L. Guerrier, J. Royer, D. S. Grierson, and H. P. Husson, “Chiral 1,4-dihydropyridine equivalents: a new approach to the asymmetric synthesis of alkaloids. The enantiospecific synthesis of (+)- and (-)-coniine and -dihydropinidine,” Journal of the American Chemical Society, vol. 105, no. 26, pp. 7754–7755, 1983. View at Google Scholar · View at Scopus
  10. J. L. Marco, J. Royer, and H. P. Husson, “Asymmetric synthesis IX1: preparation of chiral α-substituted phenethylamines,” Synthetic Communications, vol. 17, no. 6, pp. 669–676, 1987. View at Publisher · View at Google Scholar
  11. E. N. Banfi and R. Riva, Reagents for Organic Synthesis, Wiley, New York, NY, USA, 1995.
  12. M. Periasamy and M. Thirumalaikuma, “Methods of enhancement of reactivity and selectivity of sodium borohydride for applications in organic synthesis,” Journal of Organometallic Chemistry, vol. 609, pp. 137–151, 2000. View at Google Scholar
  13. C. A. Brown, “Catalytic hydrogenation. V. reaction of sodium borohydride with aqueous nickel salts. P-1 nickel boride, a convenient, highly active nickel hydrogenation catalyst,” Journal of Organic Chemistry, vol. 35, pp. 1900–1904, 1970. View at Google Scholar
  14. C. A. Brown and V. K. Ahuja, “Catalytic hydrogenation. VI. reaction of sodium borohydride with nickel salts in ethanol solution. P-2 Nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure,” Journal of Organic Chemistry, vol. 38, pp. 2226–2230, 1973. View at Google Scholar
  15. T. Satoh, N. Mitsuo, M. Nishiki, K. Nanba, and S. Suzuki, “A new powerful and selective reducing agent sodium borohydride-palladium chloride system,” Chemistry Letters, pp. 1029–1030, 1981. View at Google Scholar
  16. S. Yakabe, M. Hirano, and T. Morimoto, “Hydrogenation of alkenes with sodium borohydride and moist alumina catalyzed by nickel chloride,” Tetrahedron Letters, vol. 41, no. 35, pp. 6795–6798, 2000. View at Google Scholar · View at Scopus
  17. B. C. Ranu and S. Samanta, “Reduction of activated conjugated alkenes by the InCl3-NaBH4 reagent system,” Tetrahedron, vol. 59, no. 40, pp. 7901–7906, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. B. C. Ranu and S. Samanta, “Remarkably selective reduction of the α,β-carbon-carbon double bond in highly activated α,β,γ,δ-unsaturated alkenes by the InCl3-NaBH4 reagent system,” Journal of Organic Chemistry, vol. 68, no. 18, pp. 7130–7132, 2003. View at Publisher · View at Google Scholar
  19. P. K. Sharma, S. Kumar, P. Kumar, and P. Nielsen, “Selective reduction of mono- and disubstituted olefins by NaBH4 and catalytic RuCl3,” Tetrahedron Letters, vol. 48, no. 49, pp. 8704–8708, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. G. R. A. Adair, K. K. Kapoor, A. L. B. Scolan, and J. M. J. Williams, “Ruthenium catalysed reduction of alkenes using sodium borohydride,” Tetrahedron Letters, vol. 47, no. 50, pp. 8943–8944, 2006. View at Publisher · View at Google Scholar · View at Scopus
  21. V. V. Kalashnikov and L. G. Tomilova, “Catalytic reduction of an α,β-disubstituted alkene with sodium borohydride in the presence of tetra-tert-butylphthalocyanine complexes,” Mendeleev Communications, vol. 17, no. 6, pp. 343–344, 2007. View at Publisher · View at Google Scholar
  22. A. Aramini, L. Brinchi, R. Germani, and G. Savelli, “Reductions of α,β-unsaturated ketones by NaBH4 or NaBH4 + CoCl2: selectivity control by water or by aqueous micellar solutions,” European Journal of Organic Chemistry, no. 9, pp. 1793–1797, 2000. View at Google Scholar · View at Scopus
  23. P. W. Chum and S. E. Wilson, “Reduction of alkynes and monosubstituted alkenes with lithium aluminum hydride and titanium tetrachloride,” Tetrahedron Letters, vol. 17, no. 1, pp. 15–16, 1976. View at Google Scholar · View at Scopus
  24. E. C. Ashby and J. J. Lin, “Reduction of alkenes, alkynes and halides by lithium aluminum hydride-transition metal chloride,” Tetrahedron Letters, vol. 18, no. 51, pp. 4481–4484, 1977. View at Google Scholar · View at Scopus
  25. E. C. Ashby and J. J. Lin, “Selective reduction of alkenes and alkynes by the reagent lithium aluminum hydride-transition-metal halide,” Journal of Organic Chemistry, vol. 43, pp. 2567–2572, 1978. View at Google Scholar
  26. J. M. Tour, J. P. Cooper, and S. L. Pendalwar, “Highly selective heterogeneous palladium-catalyzed hydrogenations using triethoxysilane and water,” Journal of Organic Chemistry, vol. 55, no. 11, pp. 3452–3453, 1990. View at Google Scholar · View at Scopus
  27. J. M. Tour and S. L. Pendalwar, “Selective heterogeneous palladium-catalyzed hydrogenations of water-soluble alkenes and alkynes,” Tetrahedron Letters, vol. 31, no. 33, pp. 4719–4722, 1990. View at Publisher · View at Google Scholar · View at Scopus
  28. J. Wang, G. Song, Y. Peng, and Y. Zhu, “3-Butyl-1-methylimidazolinium borohydride ([bmim][BH4])-a novel reducing agent for the selective reduction of carbon-carbon double bonds in activated conjugated alkenes,” Tetrahedron Letters, vol. 49, no. 46, pp. 6518–6520, 2008. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, and M. Hosseini, “Palladium-catalyzed reduction of olefins with triethylsilane,” Tetrahedron Letters, vol. 44, no. 24, pp. 4579–4580, 2003. View at Publisher · View at Google Scholar · View at Scopus
  30. V. A. Likholobov, V. F. Surovikin, G. V. Plaksin, M. S. Tsekhanovich, Y. V. Surovikin, and O. N. Baklanova, “Nanostructured carbon materials for catalysis and adsorption,” Catalysis in Industry, vol. 1, pp. 11–16, 2009. View at Google Scholar
  31. S. M. Manocha, “Porous carbons,” Sādhanā, vol. 28, pp. 335–348, 2003. View at Google Scholar
  32. F.-C. Wu and R.-L. Tseng, “Preparation of highly porous carbon from fir wood by KOH etching and CO2 gasification for adsorption of dyes and phenols from water,” Journal of Colloid and Interface Science, vol. 294, no. 1, pp. 21–30, 2006. View at Publisher · View at Google Scholar
  33. H. Marsh and F. Rodriguez-Reinoso, Activated Carbon, Elsevier Science & Technology Books, 2006.
  34. R. Q. Sun, L. B. Sun, Y. Chun, and Q. H. Xu, “Catalytic performance of porous carbons obtained by chemical activation,” Carbon, vol. 46, no. 13, pp. 1757–1764, 2008. View at Publisher · View at Google Scholar · View at Scopus
  35. T. C. Miller and J. A. Holcombe, “Characterization of metal ion-exchange on modified surfaces of porous carbon,” Analytica Chimica Acta, vol. 455, pp. 233–244, 2002. View at Publisher · View at Google Scholar
  36. K. M. Thomas, “Hydrogen adsorption and storage on porous materials,” Catalysis Today, vol. 120, no. 3-4, pp. 389–398, 2007. View at Publisher · View at Google Scholar
  37. Y. Nakagawa, M. Molina-Sabio, and F. Rodríguez-Reinoso, “Modification of the porous structure along the preparation of activated carbon monoliths with H3PO4 and ZnCl2,” Microporous and Mesoporous Materials, vol. 103, no. 1–3, pp. 29–34, 2007. View at Google Scholar
  38. A. Caiazzo, S. Dalili, C. Picard, M. Sasaki, T. Siu, and A. K. Yudin, “New methods for the synthesis of heterocyclic compounds,” Pure and Applied Chemistry, vol. 76, no. 3, pp. 603–613, 2004. View at Google Scholar · View at Scopus
  39. J. Blanco, A. L. Petre, M. Yates, M. P. Martin, S. Suarez, and J. A. Martin, “Novel one-step synthesis of porous-supported catalysts by activated-carbon templating,” Advanced Materials, vol. 18, pp. 1162–1165, 2006. View at Google Scholar
  40. C. Xu, Y. Liu, and D. Yuan, “Pt and Pd supported on carbon microspheres for alcohol electrooxidation in alkaline media,” International Journal of Electrochemical Science, vol. 2, pp. 674–680, 2007. View at Google Scholar
  41. S. Kudo, T. Maki, K. Miura, and K. Mae, “High porous carbon with Cu/ZnO nanoparticles made by the pyrolysis of carbon material as a catalyst for steam reforming of methanol and dimethyl ether,” Carbon, vol. 48, no. 4, pp. 1186–1195, 2010. View at Publisher · View at Google Scholar · View at Scopus
  42. W. Shen, Z. Li, and Y. Liu, “Surface chemical functional groups modification of porous carbon,” Recent Patents on Chemical Engineering, vol. 1, pp. 27–40, 2008. View at Google Scholar
  43. J. Machnikowski, B. Grzyb, H. MacHnikowska, and J. V. Weber, “Surface chemistry of porous carbons from N-polymers and their blends with pitch,” Microporous and Mesoporous Materials, vol. 82, no. 1-2, pp. 113–120, 2005. View at Publisher · View at Google Scholar · View at Scopus
  44. M. Olivares-Marín, C. Fernández-González, A. Macías-García, and V. Gómez-Serrano, “Preparation of activated carbon from cherry stones by chemical activation with ZnCl2,” Applied Surface Science, vol. 252, no. 17, pp. 5967–5971, 2006. View at Publisher · View at Google Scholar · View at Scopus
  45. M. Kitano, K. Arai, A. Kodama et al., “Preparation of a sulfonated porous carbon catalyst with high specific surface area,” Catalysis Letters, vol. 131, no. 1-2, pp. 242–249, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. J.-B. Lee, Y.-K. Park, O.-B. Yang et al., “Synthesis of porous carbons having surface functional groups and their application to direct-methanol fuel cells,” Journal of Power Sources, vol. 158, no. 2, pp. 1251–1255, 2006. View at Publisher · View at Google Scholar
  47. A. T. Tran, V. A. Huynh, E. M. Friz, S. K. Whitney, and D. B. Cordes, “A general method for the rapid reduction of alkenes and alkynes using sodium borohydride, acetic acid, and palladium,” Tetrahedron Letters, vol. 50, no. 16, pp. 1817–1819, 2009. View at Publisher · View at Google Scholar · View at Scopus
  48. A. Shokrolahi, A. Zali, and M. H. Keshavarz, “Oxidation of organic compounds by sulfonated porous carbon and hydrogen peroxide,” Chinese Journal of Catalysis, vol. 31, no. 12, pp. 1427–1432, 2010. View at Google Scholar · View at Scopus
  49. Z. P. Sun, X. G. Zhang, H. Tong, Y. Y. Liang, and H. L. Li, “Sulfonation of ordered mesoporous carbon supported Pd catalysts for formic acid electrooxidation,” Journal of Colloid and Interface Science, vol. 337, no. 2, pp. 614–618, 2009. View at Publisher · View at Google Scholar · View at Scopus
  50. L. Calore, G. Cavinato, P. Canton, L. Peruzzo, L. Tauro, and B. Corain, “Metal catalysis with nanostructured metals supported on strongly acidic cross-linked polymer frameworks—part I. the behaviour of M2+ ions (M = Ni, Pd, Pt, Cu) supported on Rohm & Haas's resin A70 and du Pont's SAC-13, towards H2 in the solid state and NaBH4 in aqueous medium,” Reactive and Functional Polymers, vol. 70, no. 9, pp. 639–646, 2010. View at Publisher · View at Google Scholar · View at Scopus
  51. T. Harada, S. Ikeda, M. Miyazaki, and T. J. Sakata, “A simple method for preparing highly active palladium catalysts loaded on various carbon supports for liquid-phase oxidation and hydrogenation reactions,” Journal of Molecular Catalysis A, vol. 268, pp. 59–64, 2007. View at Google Scholar
  52. F. Peng, L. Zhang, H. J. Wang, P. Lv, and H. Yu, “Sulfonated carbon nanotubes as a strong protonic acid catalyst,” Carbon, vol. 43, pp. 2405–2408, 2005. View at Google Scholar
  53. C. Y. Du, T. S. Zhao, and Z. X. Liang, “Sulfonation of carbon-nanotube supported platinum catalysts for polymer electrolyte fuel cells,” Journal of Power Sources, vol. 176, no. 1, pp. 9–15, 2008. View at Publisher · View at Google Scholar · View at Scopus
  54. S. Murugesan and V. Subramanian, “Effects of acid accelerators on hydrogen generation from solid sodium borohydride using small scale devices,” Journal of Power Sources, vol. 187, no. 1, pp. 216–223, 2009. View at Publisher · View at Google Scholar · View at Scopus
  55. O. Akdim, U. B. Demirci, and P. Miele, “Acetic acid, a relatively green single-use catalyst for hydrogen generation from sodium borohydride,” International Journal of Hydrogen Energy, vol. 34, no. 17, pp. 7231–7238, 2009. View at Publisher · View at Google Scholar · View at Scopus
  56. N. Satyanarayana and M. Periasamy, “Hydroboration or hydrogenation of alkenes with CoCl2-NaBH4,” Tetrahedron Letters, vol. 25, no. 23, pp. 2501–2504, 1984. View at Google Scholar · View at Scopus
  57. J. O. Osby, S. W. Heinzman, and B. Ganem, “Studies on the mechanism of transition-metal-assisted sodium borohydride and lithium aluminum hydride reductions,” Journal of the American Chemical Society, vol. 108, no. 1, pp. 67–72, 1986. View at Google Scholar · View at Scopus
  58. U. B. Demirci and F. Garin, “PT catalysed hydrogen generation by hydrolysis of sodium tetrahydroborate,” International Journal of Green Energy, vol. 5, no. 3, pp. 148–156, 2008. View at Publisher · View at Google Scholar · View at Scopus
  59. H. C. Brown and C. A. Brown, “New highly active metal catalysts for the hydrolysis of borohydride,” Journal of American Chemical Society, vol. 84, p. 1493, 1962. View at Google Scholar
  60. G. Guella, C. Zanchetta, B. Patton, and A. Miotello, “New insights on the mechanism of palladium-catalyzed hydrolysis of sodium borohydride from11B NMR measurements,” Journal of Physical Chemistry B, vol. 110, no. 34, pp. 17024–17033, 2006. View at Publisher · View at Google Scholar · View at Scopus
  61. J. D. Roberts and M. C. Caserio, Basic Principles of Organic Chemistry, W. A. Benjamin, Inc., 2nd edition, 1977.