Table of Contents Author Guidelines Submit a Manuscript
International Journal of Photoenergy
Volume 2016, Article ID 5632613, 8 pages
http://dx.doi.org/10.1155/2016/5632613
Research Article

Photoinduced C-C Cross-Coupling of Aryl Chlorides and Inert Arenes

State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350002, China

Received 16 February 2016; Revised 27 March 2016; Accepted 7 April 2016

Academic Editor: Leonardo Palmisano

Copyright © 2016 Lele Wang 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. 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
  2. L.-C. Campeau and K. Fagnou, “Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules,” Chemical Communications, no. 12, pp. 1253–1264, 2006. View at Publisher · View at Google Scholar · View at Scopus
  3. V. Hornillos, M. Giannerini, C. Vila, M. Fañanás-Mastral, and B. L. Feringa, “Catalytic direct cross-coupling of organolithium compounds with aryl chlorides,” Organic Letters, vol. 15, no. 19, pp. 5114–5117, 2013. View at Publisher · View at Google Scholar · View at Scopus
  4. A. W. Lei, W. Liu, C. Liu, and M. Chen, “Arylation of unactivated arenes,” Dalton Transactions, vol. 39, no. 43, pp. 10352–10361, 2010. View at Publisher · View at Google Scholar · View at Scopus
  5. 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
  6. W. A. Herrmann, C. Brossmer, K. Öfele et al., “Palladacycles as structurally defined catalysts for the heck olefination of chloro- and bromoarenes,” Angewandte Chemie—International Edition, vol. 34, no. 17, pp. 1844–1848, 1995. View at Publisher · View at Google Scholar
  7. 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
  8. E. Shirakawa, K.-I. Itoh, T. Higashino, and T. Hayashi, “Tert-butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative,” Journal of the American Chemical Society, vol. 132, no. 44, pp. 15537–15539, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. A. Studer and D. P. Curran, “Organocatalysis and C-H activation meet radical- and electron-transfer reactions,” Angewandte Chemie—International Edition, vol. 50, no. 22, pp. 5018–5022, 2011. View at Publisher · View at Google Scholar
  10. W.-C. Chen, Y.-C. Hsu, W.-C. Shih et al., “Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes,” Chemical Communications, vol. 48, no. 53, pp. 6702–6704, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. S. Yanagisawa, K. Ueda, T. Taniguchi, and K. Itami, “Potassium t-butoxide alone can promote the biaryl coupling of electron-deficient nitrogen heterocycles and haloarenes,” Organic Letters, vol. 10, no. 20, pp. 4673–4676, 2008. View at Publisher · View at Google Scholar · View at Scopus
  12. C.-L. Sun, H. Li, D.-G. Yu et al., “An efficient organocatalytic method for constructing biaryls through aromatic C–H activation,” Nature Chemistry, vol. 2, pp. 1044–1049, 2010. View at Publisher · View at Google Scholar
  13. W. Liu, H. Cao, H. Zhang et al., “Organocatalysis in cross-coupling: DMEDA-catalyzed direct C−H arylation of unactivated benzene,” Journal of the American Chemical Society, vol. 132, no. 47, pp. 16737–16740, 2010. View at Publisher · View at Google Scholar · View at Scopus
  14. Y. T. Qiu, Y. H. Liu, K. Yang et al., “New ligands that promote cross-coupling reactions between aryl halides and unactivated arenes,” Organic Letters, vol. 13, no. 14, pp. 3556–3559, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. Y. J. Zhu, M. Bauer, J. Ploog, and L. Ackermann, “Late-stage diversification of peptides by metal-free C–H arylation,” Chemistry, vol. 20, no. 41, pp. 13099–13102, 2014. View at Publisher · View at Google Scholar · View at Scopus
  16. P. D. S. José, J. Steffen, and J. T. Nicholas, “Probing the photoreactivity of aryl chlorides with oxygen,” Photochemical & Photobiological Sciences, vol. 8, no. 2, pp. 210–216, 2009. View at Publisher · View at Google Scholar
  17. A. F. Littke, L. Schwarz, and G. C. Fu, “Pd/P(t-Bu)3: a mild and general catalyst for stille reactions of aryl chlorides and aryl bromides,” Journal of the American Chemical Society, vol. 124, no. 22, pp. 6343–6348, 2002. View at Publisher · View at Google Scholar · View at Scopus
  18. A. F. Littke, C. Dai, and G. C. Fu, “Versatile catalysts for the suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions,” Journal of the American Chemical Society, vol. 122, no. 17, pp. 4020–4028, 2000. View at Publisher · View at Google Scholar
  19. N. Kataoka, Q. Shelby, J. P. Stambuli, and J. F. Hartwig, “Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C–C, C–N, and C–O bond-forming cross-couplings,” Journal of Organic Chemistry, vol. 67, no. 16, pp. 5553–5566, 2002. View at Publisher · View at Google Scholar · View at Scopus
  20. M. Fagnoni, D. Dondi, D. Ravelli, and A. Albini, “Photocatalysis for the formation of the C-C bond,” Chemical Reviews, vol. 107, no. 6, pp. 2725–2756, 2007. View at Publisher · View at Google Scholar · View at Scopus
  21. G. Palmisano, V. Augugliaro, M. Pagliaro, and L. Palmisano, “Photocatalysis: a promising route for 21st century organic chemistry,” Chemical Communications, no. 33, pp. 3425–3437, 2007. View at Publisher · View at Google Scholar · View at Scopus
  22. G. E. Robinson and J. M. Vernon, “Photochemical phenylation of chlorobenzenes,” Journal of the Chemical Society D: Chemical Communications, no. 17, pp. 977–978, 1969. View at Publisher · View at Google Scholar · View at Scopus
  23. N. Kharasch, R. K. Sharma, and H. B. Lewis, “The photolysis of 4-bromobiphenyl in benzene,” Chemical Communications, no. 13, pp. 418–419, 1966. View at Publisher · View at Google Scholar · View at Scopus
  24. M. A. Chel'tsova and G. I. Nikishin, “Photolysis of aryl bromides and aryl chlorides in benzene,” Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, vol. 16, no. 2, pp. 447–448, 1967. View at Publisher · View at Google Scholar
  25. S. Protti, M. Fagnoni, and A. Albini, “Photo-cross-coupling reaction of electron-rich aryl chlorides and aryl esters with alkynes: a metal-free alkynylation,” Angewandte Chemie—International Edition, vol. 44, no. 35, pp. 5675–5678, 2005. View at Publisher · View at Google Scholar · View at Scopus
  26. G. E. Robinson and J. M. Vernon, “Photochemical reactions of chlorobenzene derivatives in benzene,” Journal of the Chemical Society C: Organic, pp. 3363–3367, 1971. View at Publisher · View at Google Scholar
  27. S. Protti, M. Fagnoni, M. Mella, and A. Albini, “Aryl Cations from aromatic halides. Photogeneration and reactivity of 4-hydroxy(methoxy)phenyl cation,” Journal of Organic Chemistry, vol. 69, no. 10, pp. 3465–3473, 2004. View at Publisher · View at Google Scholar · View at Scopus
  28. R. S. Yuan, S. L. Fan, H. X. Zhou et al., “Chlorine-radical-mediated photocatalytic activation of C−H bonds with visible light,” Angewandte Chemie, vol. 125, no. 3, pp. 1069–1073, 2013. View at Publisher · View at Google Scholar
  29. G. Zhang and I. Hua, “Cavitation chemistry of polychlorinated biphenyls:  decomposition mechanisms and rates,” Environmental Science & Technology, vol. 34, no. 8, pp. 1529–1534, 2000. View at Publisher · View at Google Scholar
  30. R. Bolton and G. H. Williams, “Homolytic arylation of aromatic and polyfluoroaromatic compounds,” Chemical Society Reviews, vol. 15, no. 2, pp. 261–289, 1986. View at Publisher · View at Google Scholar
  31. W. R. Bowman and J. M. Storey, “Synthesis using aromatic homolytic substitution—recent advances,” Chemical Society Reviews, vol. 36, no. 11, pp. 1803–1822, 2007. View at Publisher · View at Google Scholar
  32. K. Müller, C. Faeh, and F. Diederich, “Fluorine in pharmaceuticals: looking beyond intuition,” Science, vol. 317, no. 5846, pp. 1881–1886, 2007. View at Publisher · View at Google Scholar · View at Scopus
  33. A. T. Herrmann, L. L. Smith, and A. Zakarian, “A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates,” Journal of the American Chemical Society, vol. 134, no. 16, pp. 6976–6979, 2012. View at Publisher · View at Google Scholar · View at Scopus
  34. A. I. Konovalov, A. Lishchynskyi, and V. V. Grushin, “Mechanism of trifluoromethylation of aryl halides with CuCF3 and the ortho effect,” Journal of the American Chemical Society, vol. 136, no. 38, pp. 13410–13425, 2014. View at Publisher · View at Google Scholar · View at Scopus
  35. E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, and S. L. Buchwald, “The palladium-catalyzed trifluoromethylation of aryl chlorides,” Science, vol. 328, no. 5986, pp. 1679–1681, 2010. View at Publisher · View at Google Scholar · View at Scopus
  36. D. A. Nagib and D. W. C. Macmillan, “Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis,” Nature, vol. 480, no. 7376, pp. 224–228, 2011. View at Publisher · View at Google Scholar · View at Scopus