SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1380 - 1387

DOI: https://doi.org/10.6023/cjoc1110151

Reviews

Transition Metal-Catalyzed Arene Trifluoromethylation

  • L? Cuiping ,
  • Shen Qilong ,
  • Liu Dan
Expand
  • a College of Chemical Engineering, Shenyang University of Chemical Technology, Shenyang 110142;
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2011-10-15

  Revised date: 2012-02-10

  Online published: 2012-03-22

Supported by

Project supported by the Shanghai Pujiang Program (No. 11PJ1412200).

Fold

Abstract

Incorporation of trifluoromethyl group into aromatic compounds is of great importance in the medicinal, agricultural, and material sciences. Owing to the mild reaction conditions and wide substrates scope, transition metal-catalyzed trifluoromethylation of arene substrates has attracted significant attention in the past few years. Herein, the recent progress in transition metal-catalyzed trifluoromethylation of arene substrates is surveyed and summarized.

Key words： trifluoromethylation; organometallic; arene substrates; catalysis; progress

Cite this article

L? Cuiping , Shen Qilong , Liu Dan . Transition Metal-Catalyzed Arene Trifluoromethylation[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1380 -1387 . DOI: 10.6023/cjoc1110151

References

[1] Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.

[2] (a) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. (b) Kirsch, P.; Bremer, M. Angew. Chem., Int. Ed. 2000, 39, 4216.

[3] Wong. D. T.; Perry, K. W.; Bymaster, F. P. Nat. Rev. Drug Discovery 2005, 4, 764.

[4] Margot, P.; Huggenberger, F.; Amrein, J.; Weiss, B. BCPC Conf.-Pests. Dis. 1998, 2, 375.

[5] Jeschke, P.; Jeschke, P. ChemBioChem 2004, 5, 570.

[6] Reiffenrath, V.; Krause, J.; Plach, H. J.; Weber, G. Liq. Cryst. 1989, 5, 159.

[7] Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.

[8] Swarts, F. Bull. Acad. R. Med. Belg. 1892, 24, 415.

[9] (a) Boswell, G. A.; Pipka, Jr. W. C.; Schribner, R. M.; Tullock, C. W. Org. React. 1972, 21, 1 (b) Wang, C.-L. J. Org. React. 1985, 34, 319

[10] Kirsch, P. Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, Germany, 2004, p. 68.

[11] Tiers, G. V. D. J. Am. Chem. Soc. 1960, 82, 5513.

[12] Chen, Q.-Y. Li, Z.-T. J. Chem. Soc. 1993, 6, 645.

[13] Langlois, B.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525.

[14] Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98.

[15] Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411.

[16] McLoughlin, V. C. R.; Thrower, J. US 3408411, 1968 [Chem. Abstr. 1968, 68, 11002].

[17] Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 4095.

[18] Kondratenko, N. V.; Vechirko, E. P.; Yagupolskii, L. M. Synthesis, 1980 932.

[19] (a) Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014. (b) Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1986, 108, 832.

[20] Chen, Q.-Y.; Wu, S.-W. Chem. Commun. 1989, 705.

[21] Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91.

[22] Kamigata, N.; Ohtsuka, T.; Fukushima, T; Yoshida, M.; Shimizu, T. Perkin Ttrans. 1994, 1339.

[23] Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464.

[24] (a) Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600. (b) Dubinina, G. G.; Ogikubo, J.; Vicic, D. A. Organometallics 2008, 27, 6233.

[25] Hartwig. J. F. Angew. Chem., Int. Ed. 2011, 50, 3793.

[26] Weng, Z.-Q.; Lee, R.; Jia, W.-G.; Yuan, Y.-F.; Wang, W.-F.; Huang, K.-W. Organometallics 2011, 30, 3229.

[27] Olesya, A.; Tomashenko, E. C.; Escudero, A.; Belmonte, M. M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655.

[28] Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem., Int. Ed. 2011, 123, 1936.

[29] Chu, L.-L.; Qing, F.-L. Org. Lett. 2010, 12, 5060.

[30] Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174.

[31] Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909.

[32] (a) Hughes, R. P. J. Organomet. Chem. 1990, 31, 183. (b) Morrison, J. A. J. Organomet. Chem. 1993, 35, 211.

[33] (a) Matsui, K.; Tobita, E.; Ando, M.; Kondo, K. Chem. Lett. 1981, 1719. (b) Langlois, B. R.; Roques, N. J. Fluorine Chem. 2007, 128, 1318.

[34] (a) Folleas, B.; Marek, I.; Normant, J.-F.; Saint-Jalmes, L. Tetrahedron 2000, 56, 275. (b) Prakash, G. K. S.; Hu, J.; Olah, G. A. Org. Lett. 2003, 5, 3253.

[35] (a) Prakash, G. K. S.; Yudin, A. K.; Deffieux, D.; Olah, G. A. Synlett 1996, 151. (b) Huang, D.; Caulton, K. G. J. Am. Chem. Soc. 1997, 119, 3185.

[36] Knauber, T.; Arikan, F.; R鰏chenthaler, G.; Goo遝n, L. J. Chem. Eur. J. 2011, 17, 2689.

[37] Liu, T.-F.; Shen, Q. Org. Lett. 2011, 13, 2342.

[38] Xu, J.; Luo, D.-F.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300.

[39] Zhang, C.-P.; Cai, J.; Zhou, C.-B.; Wang, X.-P.; Zheng, X.; Gu, Y.-C.; Xiao, J.-C. Chem. Commun, 2011, 47, 9516.

[40] Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 4632.

[41] Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644.

[42] Nicholas, D.; Ball, J.; Gary, B.; Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 7577.

[43] Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.

[44] Wang, X.; Truesdale, L.; Yu, J. Q. J. Am. Chem. Soc. 2010, 132, 3648.

[45] Mu, X.; Chen, S.-J.; Zhen, X.-L.; Liu, G.-S. Chem. Eur. J. 2011, 17, 6039.
Options
Outlines

/

〈 〉