Zhang Ke , Xu Xiuhua , Qing Fengling . Recent Advances of Direct Trifluoromethylthiolation[J]. Chinese Journal of Organic Chemistry, 2015 , 35(3) : 556 -569 . DOI: 10.6023/cjoc201501017

[1] Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese). (卿凤翎, 有机化学, 2012, 32, 815.)
[2] Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
[3] (a) Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827. (b) Manteau, B.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140. (c) Boiko, V. N. Beilstein J. Org. Chem. 2010, 6, 880. (d) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529. (e) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214. (f) He, W.-M.; Weng, Z.-Q. Prog. Chem. 2013, 25, 1071 (in Chinese). (何伟明, 翁志强, 化学进展, 2013, 25, 1071.) (g) Toulgoat, F.; Alazet, S.; Billard, T. Eur. J. Org. Chem. 2014,, 2415. (h) Kalläne, S. I.; Braun, T. Angew. Chem., Int. Ed. 2014, 53, 931. (i) Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015. 115, 731.
[4] (a) Nodiff, E. A.; Lipschutz, S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60. (b) Suda, M.; Hino, C. Tetrahedron Lett. 1981, 22, 1997. (c) Kremsner, J. M.; Rack, M.; Pilger, C.; Kappe, C. O. Tetrahedron Lett. 2009, 50, 3665. (d) Gutmann, B.; Obermayer, D.; Reichart, B.; Prekodravac, B.; Irfan, M.; Kremsner, J. M.; Kappe, C. O. Chem. Eur. J. 2010, 16, 12182.
[5] (a) Umemoto, T.; Ishihara, S. J. Am. Chem. Soc. 1993, 115, 2156. (b) Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771. (c) Large, S.; Roques, N.; Langlois, B. R. J. Org. Chem. 2000, 65, 8848. (d) Blond, G.; Billard, T.; Langlois, B. R. Tetrahedron Lett. 2001, 42, 2473. (e) Inschauspe, D.; Sortais, J.-B.; Billard, T.; Langlois, B. R. Synlett 2003, 233. (f) Prakash, G. K. S.; Hu, J.; Olah, G. A. Org. Lett. 2003, 5, 3253. (g) Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754. (h) Prakash, G. K. S.; Weber, C.; Chacko, S.; Olah, G. A. J. Comb. Chem. 2007, 9, 920. (i) Wang, G.; Zhang, H.; Zhou, J.; Ha, C.; Pei, D.; Ding, K. Synthesis 2008, 2398. (j) Yagupolskii, L. M.; Matsnev, A. V.; Orlova, R. K.; Deryabkin, B. G.; Yagupolskii, Y. L. J. Fluorine Chem. 2008, 129, 131. (k) Cherkupally, P.; Beier, P. Tetrahedron Lett. 2010, 51, 252. (l) Riofski, M. V.; Hart, A. D.; Colby, D. A. Org. Lett. 2013, 15, 208. (m) Kawai, H.; Yuan, Z.; Tokunaga, E.; Shibata, N. Org. Biomol. Chem. 2013, 11, 1446. (n) Yamaguchi, K.; Sakagami, K.; Miyamoto, Y.; Jin, X.; Mizuno, N. Org. Biomol. Chem. 2014, 12, 9200.
[6] (a) Harris, J. F.; Stacey, F. W. J. Am. Chem. Soc. 1961, 83, 840. (b) Harris, J. F. J. Am. Chem. Soc. 1962, 84, 3148. (c) Harris, J. F. J. Org. Chem. 1966, 31, 931.
[7] Munavalli, S.; Rohrbaugh, D. K.; Rossman, D. I.; Wagner, W. G.; Durst, H. D. Phosphorus, Sulfur, Silicon Relat. Elem. 2002, 177, 1021.
[8] Haran, G.; Sharp, D. W. A. J. Chem. Soc., Perkin Trans. 1 1972, 34.
[9] Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128.
[10] Zhu, L.; Wang, G.; Guo, Q.; Xu, Z.; Zhang, D.; Wang, R. Org. Lett. 2014, 16, 5390.
[11] (a) Sheppard, W. A. J. Org. Chem. 1964, 29, 895. (b) Popov, V. I.; Kondranenko, N. V.; Haas, A. Ukr. Khim. Zh. 1983, 49, 861. (c) Rossman, D. I.; Muller, A. J.; Lewis, E. O. J. Fluorine Chem. 1991, 55, 221.
[12] (a) Andreades, S.; Harris, J. F., Jr.; Sheppard, W. A. J. Org. Chem. 1964, 29, 898. (b) Scribner, R. M. J. Org. Chem. 1966, 31, 3671. (c) Croft, T. S. Phosphorus Sulfur Relat. Elem. 1976, 2, 133.
[13] (a) Croft, T. S.; McBrady, J. J. J. Heterocycl. Chem. 1975, 12, 845. (b) Haas, A.; Hellwig, V. Chem. Ber. 1976, 109, 2475. (c) Haas, A.; Niemann, U. Chem. Ber. 1977, 110, 67. (d) Gerstenberger, M. R. C.; Haas, A.; Liebig, F. J. Fluorine Chem. 1982, 19, 461. (e) Gerstenberger, M. R. C.; Haas, A. J. Fluorine Chem. 1983, 23, 525. (f) Belanger, P. C.; Atkinson, J. G.; Rooney, C. S.; Britcher, S. F.; Remy, D. C. J. Org. Chem. 1983, 48, 3234.
[14] (a) Bayreuther, H.; Haas, A. Chem. Ber. 1973, 106, 1418. (b) Bauer, M.; Haas, A.; Muth, H. J. Fluorine Chem. 1980, 16, 129. (c) Popov, V. I.; Haas, A.; Lieb, M. J. Fluorine Chem. 1990, 47, 131.
[15] (a) Haas, A.; Lieb, M.; Zhang, Y. J. Fluorine Chem. 1985, 29, 311. (b) Haas, A.; Lieb, M.; Zhang, Y. J. Fluorine Chem. 1985, 30, 203.
[16] Bogdanowicz-Szwed, K.; Kawa?ek, B.; Lieb, M. J. Fluorine Chem. 1987, 35, 317.
[17] (a) Sharpe, T. R.; Cherkofsky, S. C.; Hewes, W. E.; Smith, D. H.; Gregory, W. A.; Haber, S. B.; Leadbetter, M. R.; Whitney, J. G. J. Med. Chem. 1985, 28, 1188. (b) South, M. S.; Van Sant, K. A. J. Heterocycl. Chem. 1991, 28, 1017. (c) Boese, R.; Haas, A.; Lieb, M.; Roeske, U. Chem. Ber. 1994, 127, 449.
[18] Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237.
[19] Ferry, A. l.; Billard, T.; Langlois, B. R.; Bacqué, E. J. Org. Chem. 2008, 73, 9362.
[20] Ferry, A.; Billard, T.; Langlois, B. R.; Bacqué, E. Angew. Chem., Int. Ed. 2009, 48, 8551.
[21] Alazet, S.; Zimmer, L.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 10814.
[22] Ferry, A.; Billard, T.; Bacqué, E.; Langlois, B. R. J. Fluorine Chem. 2012, 134, 160.
[23] Baert, F.; Colomb, J.; Billard, T. Angew. Chem., Int. Ed. 2012, 51, 10382.
[24] Alazet, S.; Ollivier, K.; Billard, T. Beilstein J. Org. Chem. 2013, 9, 2354.
[25] Yang, Y.; Jiang, X.; Qing, F.-L. J. Org. Chem. 2012, 77, 7538.
[26] Liu, J.; Chu, L.; Qing, F.-L. Org. Lett. 2013, 15, 894.
[27] (a) Xiao, Q.; Sheng, J.; Chen, Z.; Wu, J. Chem. Commun. 2013, 49, 8647. (b) Sheng, J.; Li, S.; Wu, J. Chem. Commun. 2014, 50, 578. (c) Sheng, J.; Fan, C.; Wu, J. Chem. Commun. 2014, 50, 5494. (d) Li, Y.; Li, G.; Ding, Q. Eur. J. Org. Chem. 2014, 5017. (e) Xiao, Q.; Zhu, H.; Li, G.; Chen, Z. Adv. Synth. Catal. 2014, 356, 3809.
[28] Alazet, S.; Zimmer, L.; Billard, T. Chem. Eur. J. 2014, 20, 8589.
[29] Alazet, S.; Zimmer, L.; Billard, T. J. Fluorine Chem. 2015, 171, 78.
[30] Munavalli, S.; Rohrbaugh, D. K.; Rossman, D. I.; Berg, F. J.; Wagner, G. W.; Durst, H. D. Synth. Commun. 2000, 30, 2847.
[31] Bootwicha, T.; Liu, X.; Pluta, R.; Atodiresei, I.; Rueping, M. Angew. Chem., Int. Ed. 2013, 52, 12856.
[32] Rueping, M.; Liu, X.; Bootwicha, T.; Pluta, R.; Merkens, C. Chem. Commun. 2014, 50, 2508.
[33] Pluta, R.; Nikolaienko, P.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 1650.
[34] Pluta, R.; Rueping, M. Chem. Eur. J. 2014, 20, 17315.
[35] Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316.
[36] Wang, Q.; Qi, Z.; Xie, F.; Li, X. Adv. Synth. Catal. 2015, 357, 355.
[37] Shao, X.; Wang, X.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457.
[38] Vinogradova, E. V.; Muller, P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2014, 53, 3125.
[39] Shao, X.; Liu, T. F.; Lu, L.; Shen, Q. Org. Lett. 2014, 16, 4738.
[40] (a) Hu, F.; Shao, X.; Zhu, D. H.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 6105. (b) Ma, B.; Shao, X.; Shen, Q. J. Fluorine Chem. 2015, 171, 73.
[41] (a) Wang, X.; Yang, T.; Cheng, X.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 12860. (b) Yang, T.; Shen, Q.; Lu, L. Chin. J. Chem. 2014, 32, 678.
[42] Deng, Q.-H.; Rettenmeier, C.; Wadepohl, H.; Gade, L. H. Chem. Eur. J. 2014, 20, 93.
[43] Yang, Y.-D.; Azuma, A.; Tokunaga, E.; Yamasaki, M.; Shiro, M.; Shibata, N. J. Am. Chem. Soc. 2013, 135, 8782.
[44] Zhu, X.-L.; Xu, J.-H.; Cheng, D.-J.; Zhao, L.-J.; Liu, X.-Y.; Tan, B. Org. Lett. 2014, 16, 2192.
[45] Xiang, H.; Yang, C. Org. Lett. 2014, 16, 5686.
[46] (a) Man, E. H.; Coffman, D. D.; Muetterties, E. L. J. Am. Chem. Soc. 1959, 81, 3575. (b) Harris, J. F. J. Org. Chem. 1967, 32, 2063.
[47] Tyrra, W.; Naumann, D.; Hoge, B.; Yagupolskii, Y. L. J. Fluorine Chem. 2003, 119, 101.
[48] Ye, K.-Y.; Zhang, X.; Dai, L.-X.; You, S.-L. J. Org. Chem. 2014, 79, 12106.
[49] (a) Munavalli, S.; Wagner, G. W.; Bashir Hashemi, A.; Rohrbaugh, D. K.; Durst, H. D. Synth. Commun. 1997, 27, 2847. (b) Munavalli, S.; Bashir-Hashemi, A.; Rohrbaugh, D. K.; Durst, H. D. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 435.
[50] (a) Hanack, M.; Kühnle, A. Tetrahedron Lett. 1981, 22, 3047. (b) Haas, A.; Hinsken, W. J. Fluorine Chem. 1985, 28, 303.
[51] (a) Hanack, M.; Massa, F. W. Tetrahedron Lett. 1981, 22, 557. (b) Haas, A.; Krächter, H.-U. Chem. Ber. 1988, 121, 1833.
[52] Adams, D. J.; Goddard, A.; Clark, J. H.; Macquarrie, D. J. Chem. Commun. 2000, 987.
[53] (a) Yagupolskii, L. M.; Kondratenko, N. V.; Sambur, V. P. Synthesis 1975, 721. (b) Hudlicky, M. J. Fluorine Chem. 1981, 18, 383. (c) Kondratenko, N. V.; Kolomeytsev, A. A.; Popov, V. I.; Yagupolskii, L. M. Synthesis 1985, 667. (d) Clark, J. H.; Jones, C. W.; Kybett, A. P.; McClinton, M. A.; Miller, J. M.; Bishop, D.; Blade, R. J. J. Fluorine Chem. 1990, 48, 249. (e) Clark, J. H.; Smith, H. J. Fluorine Chem. 1993, 61, 223. (f) Munavalli, S.; Hassner, A.; Rossman, D. I.; Singh, S.; Rohrbaugh, D. K.; Ferguson, C. P. J. Fluorine Chem. 1995, 73, 7. (g) Kirsch, P.; Lenges, M.; Kühne, D.; Wanczek, K.-P. Eur. J. Org. Chem. 2005, 797.
[54] Rueping, M.; Tolstoluzhsky, N.; Nikolaienko, P. Chem. Eur. J. 2013, 19, 14043.
[55] Weng, Z.; He, W.; Chen, C.; Lee, R.; Tan, D.; Lai, Z.; Kong, D.; Yuan, Y.; Huang, K.-W. Angew. Chem., Int. Ed. 2013, 52, 1548.
[56] Kong, D.; Jiang, Z.; Xin, S.; Bai, Z.; Yuan, Y.; Weng, Z. Tetrahedron 2013, 69, 6046.
[57] Tan, J.; Zhang, G.; Ou, Y.; Yuan, Y.; Weng, Z. Chin. J. Chem. 2013, 31, 921.
[58] Lin, Q.; Chen, L.; Huang, Y.; Rong, M.; Yuan, Y.; Weng, Z. Org. Biomol. Chem. 2014, 12, 5500.
[59] Wang, Z.; Tu, Q.; Weng, Z. J. Organomet. Chem. 2014, 751, 830.
[60] Rong, M.; Li, D.; Huang, R.; Huang, Y.; Han, X.; Weng, Z. Eur. J. Org. Chem. 2014, 5010.
[61] Huang, Y.; He, X.; Lin, X.; Rong, M.; Weng, Z. Org. Lett. 2014, 16, 3284.
[62] Kolomeitsev, A. A.; Chabanenko, K. Y.; Röschenthaler, G. V.; Yagupolskii, Y. L. Synthesis 1994, 145.
[63] Nikolaienko, P.; Pluta, R.; Rueping, M. Chem. Eur. J. 2014, 20, 9867.
[64] Liu, J.-B.; Xu, X.-H.; Chen, Z.-H.; Qing, F.-L. Angew. Chem., Int. Ed. 2015, 54, 897.
[65] Adams, D. J.; Clark, J. H. J. Org. Chem. 2000, 65, 1456.
[66] Wang, K.; Yun, S. Y.; Mamidipalli, P.; Lee, D. Chem. Sci. 2013, 4, 3205.
[67] Xiao, Q.; Sheng, J.; Ding, Q.; Wu, J. Eur. J. Org. Chem. 2014, 217.
[68] Hu, M.; Rong, J.; Miao, W.; Ni, C.; Han, Y.; Hu, J. Org. Lett. 2014, 16, 2030.
[69] Wang, X.; Zhou, Y.; Ji, G.; Wu, G.; Li, M.; Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2014, 3093.
[70] Lefebvre, Q.; Fava, E.; Nikolaienko, P.; Rueping, M. Chem. Commun. 2014, 50, 6617.
[71] (a) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475. (b) Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048. (c) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. (d) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
[72] Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312.
[73] Xu, C.; Shen, Q. Org. Lett. 2014, 16, 2046.
[74] Xu, J.; Mu, X.; Chen, P.; Ye, J.; Liu, G. Org. Lett. 2014, 16, 3942.
[75] Zhang, C.-P.; Vicic, D. A. J. Am. Chem. Soc. 2012, 134, 183.
[76] Kolomeitsev, A.; Médebielle, M.; Kirsch, P.; Lork, E.; Röschenthaler, G.-V. J. Chem. Soc., Perkin Trans. 1 2000, 2183.
[77] Li, S. G.; Zard, S. Z. Org. Lett. 2013, 15, 5898.
[78] (a) Glaser, C. Ber. 1869, 2, 422. (b) Hay, A. J. Org. Chem 1960, 25, 1275. (c) Hay, A. S. J. Org. Chem 1962, 27, 3320.
[79] (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933. (b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937. (c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
[80] Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
[81] Chen, C.; Xie, Y.; Chu, L.; Wang, R.-W.; Zhang, X.; Qing, F.-L. Angew. Chem., Int. Ed. 2012, 51, 2492.
[82] Chen, C.; Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 12454.
[83] Zhang, C.-P.; Vicic, D. A. Chem. Asian J. 2012, 7, 1756.
[84] Zhai, L.; Li, Y.; Yin, J.; Jin, K.; Zhang, R.; Fu, X.; Duan, C. Tetrahedron 2013, 69, 10262.
[85] Chen, C.; Xu, X.-H.; Yang, B.; Qing, F.-L. Org. Lett. 2014, 16, 3372.
[86] Zhang, K.; Liu, J.-B.; Qing, F.-L. Chem. Commun. 2014, 50, 14157.
[87] Yin, W.; Wang, Z.; Huang, Y. Adv. Synth. Catal. 2014, 356, 2998.