Mild and metal-free trifluoromethylation and pentafluoroethylation of gem-difluoroalkenes with TMSCF3 and TMSCF2CF3

Tetrahedron

Volumn 71, Issue 41, 2015, Pages 7892-7899

  Jin, Guanyi ^a   Zhang, Xuxue ^a   Fu, Dan ^a   Dai, Wenpeng ^a   Cao, Song ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

(Pentafluoroethyl)trimethylsilane; (Trifluoromethyl)trimethylsilane; gem Difluoroalkenes; Pentafluoroethylation; Trifluoromethylation

Indexed keywords

(PENTAFLUOROETHYL)TRIMETHYLSILANE; 1,1 DIARYL 2,2 DIFLUOROETHENE DERIVATIVE; ALKENE DERIVATIVE; REAGENT; TRIFLUOROMETHYL)TRIMETHYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; PENTAFLUOROETHYLATION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; TRIFLUOROMETHYLATION; X RAY CRYSTALLOGRAPHY;

EID: 84940789618     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.08.016     Document Type: Article

References (53)

1. X. Liu, M. Shimizu, and T. Hiyama Angew. Chem., Int. Ed. 43 2004 879 882
2. P. Innocenti, K.-M.J. Cheung, S. Solanki, C. Mas-Droux, F. Rowan, S. Yeoh, K. Boxall, M. Westlake, L. Pickard, T. Hardy, J.E. Baxter, G.W. Aherne, R. Bayliss, A.M. Fry, and S. Hoelder J. Med. Chem. 55 2012 3228 3241
3. M. Shimizu, Y. Takeda, M. Higashi, and T. Hiyama Angew. Chem., Int. Ed. 48 2009 3653 3656
4. J. Hong, H. Lai, Y. Liu, C. Yuan, Y. Li, P. Liu, and Q. Fang RSC Adv. 3 2013 1069 1072
5. A. Rivkin, T.-C. Chou, and S.J. Danishefsky Angew. Chem., Int. Ed. 44 2005 2838 2850
6. Y. Numata, I. Ashraful, Y. Shirai, and L. Han Chem. Commun. 47 2011 6159 6161
7. Z. Shi, J. Davies, S.-H. Jang, W. Kaminsky, and A.K.-Y. Jen Chem. Commun. 2012 7880 7882
8. C. Alonso, E.M. de Marigorta, G. Rubiales, and F. Palacios Chem. Rev. 115 2015 1847 1935
9. N. Iqbal, S. Choi, E. Kim, and E.J. Cho J. Org. Chem. 77 2012 11383 11387
10. Y. Li, L. Wu, H. Neumann, and M. Beller Chem. Commun. 2013 2628 2630
11. L. Chu, and F.-L. Qing Org. Lett. 12 2010 5060 5063
12. Z. Li, Z. Cui, and Z.-Q. Liu Org. Lett. 15 2013 406 409
13. Z. Hang, Z. Li, and Z.-Q. Liu Org. Lett. 16 2014 3648 3651
14. F.-L. Qing, X. Zhang, and Y. Peng J. Fluorine Chem. 111 2001 185 187
15. Q.-Y. Lin, X.-H. Xu, and F.-L. Qing J. Org. Chem. 79 2014 10434 10446
16. N. Iqbal, J. Jung, S. Park, and E.J. Cho Angew. Chem., Int. Ed. 53 2014 539 542
17. S. Kathiravan, and I.A. Nicholls Org. Lett. 17 2015 1874 1877
18. R. Tomita, Y. Yasu, T. Koike, and M. Akita Beilstein J. Org. Chem. 10 2014 1099 1106
19. Y. Yasu, T. Koike, and M. Akita Chem. Commun. 2013 2037 2039
20. T. Besset, D. Cahard, and X. Pannecoucke J. Org. Chem. 79 2014 413 418
21. T. Liu, and Q. Shen Org. Lett. 13 2011 2342 2345
22. Z. He, T. Luo, M. Hu, Y. Cao, and J. Hu Angew. Chem., Int. Ed. 51 2012 3944 3947
23. Z. Fang, Y. Ning, P. Mi, P. Liao, and X. Bi Org. Lett. 16 2014 1522 1525
24. X. Liu, C. Xu, M. Wang, and Q. Liu Chem. Rev. 115 2015 683 730
25. S. Barata-Vallejo, M.R. Torviso, B. Lantanño, S.M. Bonesi, and A. Postigo J. Fluorine Chem. 161 2014 134 141
26. G.K.S. Prakash, and A.K. Yudin Chem. Rev. 97 1997 757 786
27. N. Boechat, and M.M. Bastos Curr. Org. Synth. 7 2010 403 413
28. Q. Liu, Y. Wu, P. Chen, and G. Liu Org. Lett. 15 2013 6210 6213
29. R. Krishnamurti, D.R. Bellew, and G.K.S. Prakash J. Org. Chem. 56 1991 984 989
30. G.K.S. Prakash, C. Panja, H. Vaghoo, V. Surampudi, R. Kultyshev, M. Mandal, G. Rasul, T. Mathew, and G.A. Olah J. Org. Chem. 71 2006 6806 6813
31. A. Hafnera, and S. Bräse Adv. Synth. Catal. 353 2011 3044 3048
32. E.J. Cho, and S.L. Buchwald Org. Lett. 13 2011 6552 6555
33. Z. Mao, F. Huang, H. Yu, J. Chen, Z. Yu, and Z. Xu Chem. - Eur. J. 20 2014 3439 3445
34. K. Fuchibe, M. Takahashi, and J. Ichikawa Angew. Chem., Int. Ed. 51 2012 12059 12062
35. T. Fujita, K. Sakoda, M. Ikeda, M. Hattori, and J. Ichikawa Synlett 2013 57 60
36. J. Ichikawa, Y. Wada, M. Fujiwara, and K. Sakoda Synthesis 13 2002 1917 1936
37. J. Wiedemann, T. Heiner, G. Mloston, G.K.S. Prakash, and G.A. Olah Angew. Chem., Int. Ed. 37 1998 820 821
38. G.K.S. Prakash, R. Krishnamurti, and G.A. Olah J. Am. Chem. Soc. 111 1989 393 395
39. R. Hübinger, and G. Pawelke J. Fluorine Chem. 115 2002 115 118
40. T. Kitazume, and S. Nakajima J. Fluorine Chem. 125 2004 1447 1449
41. L.S. German, E.I. Mysov, and E.G. Ter-Gabriélyan Russ. Chem. B 2 1990 491 492
42. D.J. Burton, and S.W. Hansen ARKIVOC 8 2010 41 54
43. Y. Xiong, X. Zhang, T. Huang, and S. Cao J. Org. Chem. 79 2014 6395 6402
44. W. Dai, J. Xiao, G. Jin, J. Wu, and S. Cao J. Org. Chem. 79 2014 10537 10546
45. G. Jin, J. Zhang, W. Wu, and S. Cao J. Fluorine Chem. 168 2014 240 246
46. M. Wang, F. Liang, Y. Xiong, and S. Cao RSC Adv. 5 2015 11996 11999
47. X. Zhang, W. Dai, W. Wu, and S. Cao Org. Lett. 17 2015 2708 2711
48. H. Lu, and R.B. Silverman J. Med. Chem. 49 2006 7404 7412
49. M.E. Pierce, D.J. Carini, G.F. Huhn, G.J. Wells, and J.F. Arnett J. Org. Chem. 58 1993 4642 4645
50. A. Lishchynskyi, Z. Mazloomi, and V.V. Grushin Synlett 2015 45 50
51. P.G. Gassman, and N.J. O'Reilly J. Org. Chem. 52 1987 2481 2490
52. A. Hafner, A. Bihlmeier, M. Nieger, W. Klopper, and S. Bräse J. Org. Chem. 78 2013 7938 7948
53. M. Hu, Z. He, B. Gao, L. Li, C. Ni, and J. Hu J. Am. Chem. Soc. 135 2013 17302 17305