Recent advances in trifluoromethylthiolation using nucleophilic trifluoromethylthiolating reagents

Tetrahedron Letters

Volumn 57, Issue 13, 2016, Pages 1397-1409

  Zheng, Huidong ^a   Huang, Yangjie ^a   Weng, Zhiqiang ^a  

^a FUZHOU UNIVERSITY   (China)

Author keywords

Nucleophilic; Reagent; Trifluoromethyl thioethers; Trifluoromethylthiolation

Indexed keywords

LIPOPHILICITY; SYNTHESIS;

EID: 84959513984     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2016.02.073     Document Type: Review

References (81)

1. A. Tressaud, and G. Haufe Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals 2008 Elsevier London
2. I. Ojima Fluorine in Medicinal Chemistry and Chemical Biology 2009 John Wiley & Sons Ltd
3. J. Wang, M. Sánchez-Roselló, J.L. Aceña, C. del Pozo, A.E. Sorochinsky, S. Fustero, V.A. Soloshonok, and H. Liu Chem. Rev. 114 2013 2432
4. X.-H. Xu, K. Matsuzaki, and N. Shibata Chem. Rev. 115 2015 731
5. T. Nakajima, and H. Groult Fluorinated Materials for Energy Conversion 2005 Elsevier London
6. D. O'Hagan, and D.B. Harper J. Fluorine Chem. 100 1999 127
7. A. Leo, C. Hansch, and D. Elkins Chem. Rev. 71 1971 525
8. L.M. Yagupol'skii, A.Y. Ilchenko, and N.V. Kondratenko Russ. Chem. Rev. 43 1974 32
9. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165
10. P.B. Curtis-Prior, and M. Prouteau Int. J. Obes. 7 1983 575
11. N. Aswapokee, and H.C. Neu Antimicrob. Agents Chemother. 15 1979 444
12. L.M. Yagupolskii, I.I. Maletina, K.I. Petko, D.V. Fedyuk, R. Handrock, S.S. Shavaran, B.M. Klebanov, and S. Herzig J. Fluorine Chem. 109 2001 87
13. P. Pommier, A. Keita, S. Wessel-Robert, B. Dellac, and H.C. Mundt Rev. Med. Vet. (Toulouse, Fr.) 154 2003 41
14. F. Colliot, K.A. Kukorowski, D.W. Hawkins, and D.A. Roberts Brighton Crop Prot. Conf. Pests Dis. 1992 29
15. N. Hamon, R. Shaw, and H. Yang Proc. Beltwide Cotton Conf. 1996 759
16. V.N. Boiko Beilstein J. Org. Chem. 6 2010 880
17. A. Tlili, and T. Billard Angew. Chem., Int. Ed. 52 2013 6818
18. W. He, and Z. Weng Prog. Chem. 25 2013 1071
19. F. Toulgoat, S. Alazet, and T. Billard Eur. J. Org. Chem. 2014 2415
20. C. Ni, M. Hu, and J. Hu Chem. Rev. 115 2015 765
21. K. Zhang, X. Xu, and F. Qing Youji Huaxue 35 2015 556
22. F. Baert, J. Colomb, and T. Billard Angew. Chem., Int. Ed. 51 2012 10382
23. X. Shao, X. Wang, T. Yang, L. Lu, and Q. Shen Angew. Chem., Int. Ed. 52 2013 3457
24. T. Bootwicha, X. Liu, R. Pluta, I. Atodiresei, and M. Rueping Angew. Chem., Int. Ed. 52 2013 12856
25. E.H. Man, D.D. Coffman, and E.L. Muetterties J. Am. Chem. Soc. 81 1959 3575
26. S. Munavalli, G.W. Wagner, A.B. Hashemi, D.K. Rohrbaugh, and H.D. Durst Synth. Commun. 27 1997 2847
27. W. Tyrra, D. Naumann, B. Hoge, and Y.L. Yagupolskii J. Fluorine Chem. 119 2003 101
28. J.F. Harris J. Org. Chem. 31 1966 931
29. O. Scherer Angew. Chem. 52 1939 457
30. B. Langlois, and M. Desbois Ann. Chim. (Paris) 9 1984 729
31. L. Saint-Jalmes J. Fluorine Chem. 127 2006 85
32. C. Pooput, M. Medebielle, and W.R. Dolbier Org. Lett. 6 2004 301
33. C. Pooput, W.R. Dolbier, and M. Médebielle J. Org. Chem. 71 2006 3564
34. I. Kieltsch, P. Eisenberger, and A. Togni Angew. Chem., Int. Ed. 46 2007 754
35. S.I. Kalläne, and T. Braun Angew. Chem., Int. Ed. 53 2014 9311
36. G.S. Ponticello, R.D. Hartman, W.C. Lumma Jr., and J.J. Baldwin J. Org. Chem. 44 1979 3080
37. A. Haas, and K.W. Kempf Tetrahedron 40 1984 4963
38. W.J. Middleton J. Org. Chem. 49 1984 919
39. H.J. Emeléus, and D.E. MacDuffie J. Chem. Soc. 1961 2597
40. M. Hanack, and F.W. Massa Tetrahedron Lett. 22 1981 557
41. M. Jiang, F. Zhu, H. Xiang, X. Xu, L. Deng, and C. Yang Org. Biomol. Chem. 13 2015 6935
42. D.J. Adams, and J.H. Clark J. Org. Chem. 65 2000 1456
43. G. Teverovskiy, D.S. Surry, and S.L. Buchwald Angew. Chem., Int. Ed. 50 2011 7312
44. J. Xu, X. Mu, P. Chen, J. Ye, and G. Liu Org. Lett. 16 2014 3942
45. P. Saravanan, and P. Anbarasan Adv. Synth. Catal. 357 2015 3521
46. M. Hu, J. Rong, W. Miao, C. Ni, Y. Han, and J. Hu Org. Lett. 16 2014 2030
47. X. Wang, Y. Zhou, G. Ji, G. Wu, M. Li, Y. Zhang, and J. Wang Eur. J. Org. Chem. 2014 3093
48. J.B. Liu, X.H. Xu, Z.H. Chen, and F.L. Qing Angew. Chem., Int. Ed. 54 2015 897
49. K.-P. Wang, S.Y. Yun, P. Mamidipalli, and D. Lee Chem. Sci. 4 2013 3205
50. Q. Xiao, J. Sheng, Q. Ding, and J. Wu Eur. J. Org. Chem. 2014 217
51. A. Haas, and H.-U. Krächter Chem. Ber. 1988 1833 121
52. J.H. Clark, C.W. Jones, A.P. Kybett, and M.A. McClinton J. Fluorine Chem. 48 1990 249
53. D.C. Remy, K.E. Rittle, C.A. Hunt, and M.B. Freedman J. Org. Chem. 41 1976 1644
54. L.M. Yagupolskii, N.V. Kondratenko, and V.P. Sambur Synthesis 1975 721
55. N.V. Kondratenko, A.A. Kolomeytsev, V.I. Popov, and L.M. Yagupolskii Synthesis 1985 667
56. Y. Yang, L. Xu, S. Yu, X. Liu, Y. Zhang, and D.A. Vicic Chem. Eur. J. 22 2016 858
57. D.J. Adams, A. Goddard, J.H. Clark, and D.J. Macquarrie Chem. Commun. 2000 987
58. P. Nikolaienko, R. Pluta, and M. Rueping Chem. Eur. J. 20 2014 9867
59. Z. Weng, W. He, C. Chen, R. Lee, D. Tan, Z. Lai, D. Kong, Y. Yuan, and K.-W. Huang Angew. Chem., Int. Ed. 52 2013 1548
60. M. Zhang, and Z. Weng Adv. Synth. Catal. 358 2016 386
61. Y. Huang, J. Ding, C. Wu, H. Zheng, and Z. Weng J. Org. Chem. 80 2015 2912
62. P. Zhu, X. He, X. Chen, Y. You, Y. Yuan, and Z. Weng Tetrahedron 70 2014 672
63. C. Hou, X. Lin, Y. Huang, Z. Chen, and Z. Weng Synthesis 47 2015 969
64. Q. Lin, L. Chen, Y. Huang, M. Rong, Y. Yuan, and Z. Weng Org. Biomol. Chem. 12 2014 5500
65. D. Kong, Z. Jiang, S. Xin, Z. Bai, Y. Yuan, and Z. Weng Tetrahedron 69 2013 6046
66. Y. Huang, X. He, X. Lin, M. Rong, and Z. Weng Org. Lett. 16 2014 3284
67. J. Li, F.-F. Xie, P. Wang, Q.-Y. Wu, W.-D. Chen, J. Ren, and B.-B. Zeng Tetrahedron 71 2015 5520
68. Y. Huang, X. He, H. Li, and Z. Weng Eur. J. Org. Chem. 2014 7324
69. J. Tan, G. Zhang, Y. Ou, Y. Yuan, and Z. Weng Chin. J. Chem. 31 2013 921
70. M. Rong, D. Li, R. Huang, Y. Huang, X. Han, and Z. Weng Eur. J. Org. Chem. 2014 5010
71. J. Li, P. Wang, F.-F. Xie, X.-G. Yang, X.-N. Song, W.-D. Chen, J. Ren, and B.-B. Zeng Eur. J. Org. Chem. 2015 3568
72. Z. Wang, Q. Tu, and Z. Weng J. Organomet. Chem. 751 2014 830
73. M.M. Kremlev, W. Tyrra, D. Naumann, and Y.L. Yagupolskii Tetrahedron Lett. 45 2004 6101
74. C.-P. Zhang, and D.A. Vicic J. Am. Chem. Soc. 134 2012 183
75. G. Yin, I. Kalvet, U. Englert, and F. Schoenebeck J. Am. Chem. Soc. 137 2015 4164
76. G. Yin, I. Kalvet, and F. Schoenebeck Angew. Chem., Int. Ed. 54 2015 6809
77. A.B. Durr, G. Yin, I. Kalvet, F. Napoly, and F. Schoenebeck Chem. Sci. 7 2016 1076
78. C. Matheis, V. Wagner, and L.J. Goossen Chem. Eur. J. 22 2016 79
79. K.-Y. Ye, X. Zhang, L.-X. Dai, and S.-L. You J. Org. Chem. 79 2014 12106
80. J. Zheng, L. Wang, J.-H. Lin, J.-C. Xiao, and S.H. Liang Angew. Chem., Int. Ed. 54 2015 13236
81. J. Zheng, J.-H. Lin, J. Cai, and J.-C. Xiao Chem. Eur. J. 19 2013 15261