Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Transition Metal-Catalyzed Ortho-Functionalization in Organic Synthesis

  • Park, Young-Jun (Center for Bioactive Molecular Hybrid (CBMH), Department of Chemistry, Yonsei University) ;
  • Jun, Chul-ho (Center for Bioactive Molecular Hybrid (CBMH), Department of Chemistry, Yonsei University)
  • Published : 2005.06.20
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Abstract

Recent progress in the filed of transition-metal mediated C-H bond activation has had a great influence on organic synthesis. Among such transition-metal catalyzed reactions, ortho-functionalization via the chelationassisted strategy has been paid great attentions as one of the powerful methodologies for converting aromatic compounds into ones that are more functionalized at the exclusively ortho-position. In this context, various transition metal-catalyzed ortho-functionalizations such as alkylation, alkenylation, silylation and carbonylation are described briefly and their prospects are suggested.

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References

  1. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077 https://doi.org/10.1002/adsc.200303094
  2. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731 https://doi.org/10.1021/cr0104330
  3. Dyker, G. Angew. Chem. Int. Ed. 1999, 38, 1698 https://doi.org/10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO;2-6
  4. Jun, C.-H.; Lee, J. H. Pure Appl. Chem. 2004, 76, 577 https://doi.org/10.1351/pac200476030577
  5. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529 https://doi.org/10.1038/366529a0
  6. Freidel, C.; Crafts, J. M. Bull. Soc. Chim. Fr. 1877, 27, 530
  7. Kerr, J. A. In CRC Handbook of Chemistry and Physics, 71st ed.; Lide, D. R. Ed.; CRC: Boston, 1990; pp 9-95
  8. Bishop III, K. C. Chem. Rev. 1976, 76, 461 and references therein https://doi.org/10.1021/cr60302a003
  9. Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728 https://doi.org/10.1021/ja00270a036
  10. Kakiuchi, F.; Sonoda, M.; Tsujimoto, T.; Chatani, N.; Murai, S. Chem. Lett. 1999, 19
  11. Uchimaru, Y. Chem. Commun. 1999, 1133
  12. Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 6616 https://doi.org/10.1021/ja990702s
  13. Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K.-W. Angew. Chem. Int. Ed. 2000, 39, 3440 https://doi.org/10.1002/1521-3773(20001002)39:19<3440::AID-ANIE3440>3.0.CO;2-1
  14. Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 8, 485 https://doi.org/10.1002/1521-3765(20020118)8:2<485::AID-CHEM485>3.0.CO;2-1
  15. Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2003, 5, 1301 https://doi.org/10.1021/ol034228d
  16. Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192 https://doi.org/10.1021/ja0394986
  17. Jun, C.-H.; Moon, C. W.; Kim, Y.-M.; Lee, H.; Lee, J. H. Tetrahedron Lett. 2002, 43, 4233 https://doi.org/10.1016/S0040-4039(02)00769-4
  18. Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687 https://doi.org/10.1021/ol048095n
  19. Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211 https://doi.org/10.1021/jo980584b
  20. Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586 https://doi.org/10.1021/ja0176907
  21. Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681
  22. Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C.-H. Org. Lett. 2003, 5, 2759 https://doi.org/10.1021/ol035083d
  23. Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655 https://doi.org/10.1016/S0040-4039(00)00238-0
  24. Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem. Int. Ed. 2003, 42, 112 https://doi.org/10.1002/anie.200390037
  25. Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698 https://doi.org/10.1021/ja029273f
  26. Park, Y. J.; Jo, E.-A.; Jun, C.-H. Chem. Commun. 2005, 1185
  27. Kakiuchi, F.; Igi, K.; Matsumoto, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 422
  28. Kakiuchi, F.; Igi, K.; Matsumoto, M.; Hayamizu, T.; Chatani, N.; Murai, S. Chem. Lett. 2002, 396
  29. Kakiuchi, F.; Matsumoto, M.; Sonoda, M.; Fukuyama, T.; Chatani, N.; Murai, S.; Furukawa, N.; Seki, Y. Chem. Lett. 2000, 750
  30. Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888 https://doi.org/10.1021/ja00040a078
  31. Moore, E. J.; Pretzer, W. R. US Patent 5,081,250, 1992
  32. Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647 https://doi.org/10.1021/jo970697f

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