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Transition Metal-Catalyzed C—H Trifluoromethylation

  • Pan Fei ,
  • Shi Zhangjie
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  • a Beijing National Laboratory of Molecular Science (BNLMS, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China;
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Received date: 2012-07-30

  Online published: 2012-08-15

Supported by

Project supported by the “973” Project from the Ministry of Science and Technology of the People’s Republic of China (No. 2009CB825300) and National Natural Science Foundation of China (Nos. 20925207, 21002001).

Abstract

In recent years, transition metal-catalyzed C—H trifluoromethylation has been well developed, which is mainly focused on the terminal alkyne C(sp)—H, aromatic and heterocyclic C(sp2)—H and allylic C(sp3)—H trifluoromethylation. This paper briefly overviews the latest developments in this field, the characteristics of various types of reaction, as well as the facing challenges and future direction.

Cite this article

Pan Fei , Shi Zhangjie . Transition Metal-Catalyzed C—H Trifluoromethylation[J]. Acta Chimica Sinica, 2012 , 70(16) : 1679 -1681 . DOI: 10.6023/A12040135

References

[1] (a) Bott, G.; Field, L. D.; Sternhell, S. J. Am. Chem. Soc. 1980, 102, 5618;   
(b) Curran, D. P. Angew. Chem. Int Ed. 1998, 37, 1174;   
(c) Clark, H. C.; Tsai, J. H. J. Organomet. Chem. 1967, 7, 515.  
[2] (a) Chen, Q.-Y.; Wu, S.-W. J. Chem. Soc. Perk. 1. 1989, 2385;   
(b) Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91;   
(c) Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2002, 327;
(d) Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600;
(e) Dubinina, G. G.; Ogikubo, J.; Vicic, D. A. Organometallics 2008, 27, 6233;   
(f) Oishi, M.; Kondo, H. Chem. Commun. 2009, 1909;   
(g) Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.  
[3] (a) Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648;   
(b) Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682.  
[4] (a) Mu, X.; Chen, S.; Zhen, X.; Liu, G.-S. Chem.-Eur. J. 2011, 17, 6039;   
(b) Chu, L.-L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298.  
[5] Liu, T.-F.; Shao, X.-X.; Wu, Y.-M.; Shen, Q.-L. Angew. Chem. Int. Ed. 2012, 51, 540.  
[6] 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, 15330.
[7] (a) Parsons, A. T.; Buchwald, S. L. Angew. Chem. Int. Ed. 2011, 50, 9120;   
(b) Wang, X.; Ye, Y.-X.; Zhang, S.-N.; Feng, J.-J.; Xu, Y.; Zhang, Y.; Wang, J.-B. J. Am. Chem. Soc. 2011, 133, 16410.  
[8] (a) Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875;   
(b) Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 4986;   
(c) Pham, P. V.; MacMillan, D. W. C. Angew. Chem. Int. Ed. 2011, 50, 6119;   
(d) Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.  
[9] (a) Chu, L.-L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262;   
(b) Jiang, X.-L.; Chu, L.-L.; Qing, F.-L. J. Org. Chem. 2012, 77, 1251.  
[10] Zanardi, A.; Novikov, M. A.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 20901.  
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