Recent Advances of Trifluoromethylation

doi:10.6023/cjoc1202021

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (05): 815-824.DOI: 10.6023/cjoc1202021 Previous Articles Next Articles

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从三氟甲基化反应的近年进展看有机氟化学的发展趋势

卿凤翎^a

a 中国科学院上海有机化学研究所有机氟化学重点实验室，上海200032;
b 东华大学化学化工与生物工程学院，上海201620

收稿日期:2012-02-02 修回日期:2012-03-01 发布日期:2012-04-10
通讯作者: 卿凤翎 E-mail:flq@mail.sioc.ac.cn
基金资助:
国家自然科学基金(Nos. 21072028, 20832008)和国家重点基础研究发展计划(No. 2012CB21600)资助项目.

Recent Advances of Trifluoromethylation

Qing Feng-Ling^a

a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
b College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620

Received:2012-02-02 Revised:2012-03-01 Published:2012-04-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21072028, 20832008) and the National Basic Research Program of China (No. 2012CB21600).

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Qing Feng-Ling. Recent Advances of Trifluoromethylation[J]. Chin. J. Org. Chem., 2012, 32(05): 815-824.

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References

[1] (a) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317,1881. (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.

[2] Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.

[3] (a) Allemann, O.; Duttwyler, S.; Romanato, P.; Baldridge, K. K.; Siegel, J. S. Science 2011, 332, 574. (b) Choi, J.; Wang, D. Y.; Kundu, S.; Choliy, Y.; Emge, T. J.; Krogh-Jespersen, K.; Goldman, A. Science 2011, 332, 1545. (c) Lee, E.; Kamlet, A. S.; Powers, D. C.; Neumann, C. N.; Boursalian, G. B.; Furuya, T.; Choi, D. C.; Hooker, J. M.; Ritter, T. Science 2011, 334, 639. (d) Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science 2011, 334, 1681.

[4] (a) Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V. D.; Roy, S. Tetrahedron 2011, 67, 2161. (b) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.

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

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

[7] Nagib, D. A.; MacMillan, D. W. C. Natrue 2011, 480, 224.

[8] (a) Kamigata, N.; Fuukushima, T.; Yoshida, M. Chem. Lett., 1990, 19, 649. (b) Huang, W. Y.; Lu, L. Chinese J. Chem. 1992, 10, 268.

[9] Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398.

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

[11] Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; García-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661.

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

[13] Cho, E. J.; Buchwald, S. L. Org. Lett, 2011, 13, 6552.

[14] (a) Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878. (b) Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 16482. (c) Ball, N. D.; Gary, J. B.; Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 7577.

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

[16] McLaughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921.

[17] Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 10, 4095.

[18] Wiemers, D. M.; Burton, D. J. J. Am. Chem. Soc. 1986, 108, 832.

[19] Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600.

[20] Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem. Int. Ed. 2011, 50, 3793.

[21] Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem. Int. Ed. 2012, 51, 536.

[22] Tomashenko, O. A.; Escudero-Adán, E. C.; Belmonte, M. M.; Grushin, V. V. Angew. Chem. Int. Ed. 2011, 50, 7655.

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

[24] Knauber, T.; Arikan, F.; Roschenthaler, G.-V.; Gooβen, L. J. Chem. Eur. J. 2011, 17, 2689.

[25] Khan, B. A.; Buba, A. E.; Gooβen, L. J. Chem. Eur. J. 2012, 18, 1577.

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

[27] Parson, A. T.; Buchwald, S. L. Angew. Chem. Int. Ed. 2011, 50, 9120.

[28] Nagib, D. A.; Scott. M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875.

[29] Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 4986.

[30] Chen, Q. Y. J. Fluorine Chem. 1995, 72, 241.

[31] Chen, Q. Y.; Wu, S. W. J. Chem. Soc., Chem. Commun. 1989, 705.

[32] Qiu, S.; Xu, T.; Zhou, J.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2010, 132, 2856.

[33] Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem. Eur. J. 2011, 17, 6039.

[34] Mu, X.; Wu, T.; Wang, H. Y.; Guo, Y.; Liu, G. J. Am. Chem. Soc. 2012, 134, 878.

[35] Zhao, Y.; Hu, J. Angew. Chem. Int. Ed. 2012, 51, 1033.

[36] Zhang, C. P.; Wang, Z. L.; Chen, Q. Y.; Zhang, C. T.; Gu. Y. C. Xiao, J. C. Angew. Chem. Int. Ed. 2011, 50, 1896.

[37] Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K. W. Organometallics 2011, 30, 3229.

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

[39] Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342

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

[41] Liu, T.; Shao, X.; Wu, Y.; Shen, Q. Angew. Chem. Int. Ed. 2012, 51, 555.

[42] Xu, J.; Fu, Y.; Luo, D. F.; Jiang, Y. Y.; Xiao, B.; Liu, Z. J.; Gong, T. J.; Liu. L. J. Am. Chem. Soc. 2011, 133, 15300.

[43] Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410.

[44] Chu, L.; Qing, F. L. J. Am. Chem. Soc. 2010, 132, 7262.

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

[46] Zhang, K.; Qiu, X. L.; Huang, Y.; Qing, F. L. Eur. J. Org. Chem. 2012, 58.

[47] Jiang, X.; Chu, L.; Qing, F. L. J. Org. Chem. 2012, 77, 1251.

[48] Chu, L.; Qing, F. L. J. Am. Chem. Soc. 2012, 134, 1298.

[49] Chu, L.; Qing, F. L. Chem. Commun. 2010, 46, 6285.

[50] Chen, C.; Xie, Y.; Chu, L.; Wang, R. W.; Zhang, X.; Qing, F. L. Angew. Chem. Int. Ed., 2012, DOI: 10.1002/anie.201108663

[51] (a) Cai, L.; Lu, S.; Pike, V. W. Eur. J. Org. Chem. 2008, 2853. (b)Littich, R.; Scott, P. J. H. Angew. Chem. Int. Ed., 2012, 51, 1106.

[52] Furuya, T.; Klein, J. E. M. N.; Ritter, T. Synthesis 2010, 1804

从三氟甲基化反应的近年进展看有机氟化学的发展趋势

Recent Advances of Trifluoromethylation

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