Rh(III)-Catalyzed Trifluoromethylthiolation of Indoles via C-H Activation

Journal of Organic Chemistry

Volumn 80, Issue 16, 2015, Pages 8361-8366

  Wang, Qiang ^a   Xie, Fang ^a   Li, Xingwei ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL ACTIVATION; RHODIUM;

C-H ACTIVATION; C-S COUPLINGS; EFFICIENT CATALYSTS; FUNCTIONALIZED; HETEROCYCLES;

RHODIUM COMPOUNDS;

FUNCTIONAL GROUP; INDOLE DERIVATIVE; N TRIFLUOROMETHYLTHIOSACCHARIN; POLYCYCLIC AROMATIC HYDROCARBON; REAGENT; RHODIUM; UNCLASSIFIED DRUG; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MESYLIC ACID DERIVATIVE; N-TRIFLUOROMETHYLTHIOSACCHARIN; SACCHARIN;

ARTICLE; CATALYST; CHEMICAL REACTION; COVALENT BOND; ELECTRON; ELECTROPHILICITY; NUCLEOPHILICITY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE; TRIFLUOROMETHYLTHIOLATION; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; STEREOISOMERISM;

CATALYSIS; HYDROGEN BONDING; INDICATORS AND REAGENTS; INDOLES; MESYLATES; MOLECULAR STRUCTURE; RHODIUM; SACCHARIN; STEREOISOMERISM;

EID: 84940210737     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00940     Document Type: Article

References (84)

1. Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525 10.1021/cr60274a001
2. Smart, B. E. J. Fluorine Chem. 2001, 109, 3 10.1016/S0022-1139(01)00375-X
3. Dolbier, W. R., Jr. J. Fluorine Chem. 2005, 126, 157 10.1016/j.jfluchem.2004.09.033
4. Hird, M. Chem. Soc. Rev. 2007, 36, 2070 10.1039/b610738a
5. Manteau, B.; Pazenok, S.; Vors, J. P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140 10.1016/j.jfluchem.2009.09.009
6. Becker, A. Inventory of Industrial Fluoro-Biochemicals; Eyrolles: Paris, 1996.
7. Isanbor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303 10.1016/j.jfluchem.2006.01.011
8. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881 10.1126/science.1131943
9. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320 10.1039/B610213C
10. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359 10.1021/jm800219f
11. Begue, J.-P. D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley: Hoboken, NJ, 2008.
12. Ojima, I., Ed.; Fluorine in Medicinal Chemistry and Chemical Biology; Wiley: Chichester, U.K., 2009.
13. Boiko, V. N. Beilstein J. Org. Chem. 2010, 6, 880 10.3762/bjoc.6.88
14. Tlili, A.; Billard, T. Angew. Chem., Int. Ed. 2013, 52, 6818 10.1002/anie.201301438
15. Toulgoat, F.; Alazet, S.; Billard, T. Eur. J. Org. Chem. 2014, 2014, 2415 10.1002/ejoc.201301857
16. Ma, B.; Shao, X.; Shen, Q. J. Fluorine Chem. 2015, 171, 73 10.1016/j.jfluchem.2014.09.011
17. Yarovenko, N. N.; Vasileva, A. S. J. Gen. Chem. USSR (Engl. Transl.) 1958, 28, 2537
18. Nodiff, E. A.; Lipschutz, S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60 10.1021/jo01071a018
19. Feiring, A. E. J. Org. Chem. 1979, 44, 2907 10.1021/jo01330a017
20. Boiko, V. N.; Shchupak, G. M.; Yagupolskii, L. M. Zh. Org. Khim. 1977, 13, 1057
21. Wakselman, C.; Tordeux, M. J. Org. Chem. 1985, 50, 4047 10.1021/jo00221a017
22. Wakselman, C.; Tordeux, M.; Clavel, J.-L.; Langlois, B. R. J. Chem. Soc., Chem. Commun. 1991, 993 10.1039/c39910000993
23. Ignatev, N. V.; Datsenko, S. D.; Yagupolskii, L. M. Zh. Org. Khim. 1991, 27, 905
24. Koshechko, V. G.; Kiprianova, L. A.; Fileleeva, L. I. Tetrahedron Lett. 1992, 33, 6677 10.1016/S0040-4039(00)61016-X
25. Movchun, V. N.; Kolomeitsev, A. A.; Yagupolskii, L. M. J. Fluorine Chem. 1995, 70, 255 10.1016/0022-1139(94)03124-I
26. Billard, T.; Langlois, B. R. Tetrahedron Lett. 1996, 37, 6865 10.1016/0040-4039(96)01530-4
27. Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 9057 10.1016/S0040-4039(96)02127-2
28. Billard, T.; Blond, G.; Langlois, B. R. Tetrahedron Lett. 1997, 38, 65 10.1016/S0040-4039(96)02216-2
29. Billard, T.; Roques, N.; Langlois, B. R. J. Org. Chem. 1999, 64, 3813 10.1021/jo980649a
30. Large, S.; Roques, N.; Langlois, B. R. J. Org. Chem. 2000, 65, 8848 10.1021/jo000150s
31. Blond, G.; Billard, T.; Langlois, B. R. Tetrahedron Lett. 2001, 42, 2473 10.1016/S0040-4039(01)00225-8
32. Pooput, C.; Dolbier, W. R.; Mdebielle, M. J. Org. Chem. 2006, 71, 3564 10.1021/jo060250j
33. Yagupolskii, L. M.; Kondratenko, N. V.; Sambur, V. P. Synthesis 1975, 1975, 721 10.1055/s-1975-23905
34. Remy, D. C.; Rittle, K. E.; Hunt, C. A.; Freedman, M. B. J. Org. Chem. 1976, 41, 1644 10.1021/jo00871a037
35. 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 10.1016/S0022-1139(00)80437-6
36. Clark, J. H.; Tavener, S. J. J. Fluorine Chem. 1997, 85, 169 10.1016/S0022-1139(97)00057-2
37. Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312 10.1002/anie.201102543
38. Zhang, C. P.; Vicic, D. A. J. Am. Chem. Soc. 2012, 134, 183 10.1021/ja210364r
39. Chen, C.; Xie, Y.; Chu, L.; Wang, R. W.; Zhang, X.; Qing, F. L. Angew. Chem., Int. Ed. 2012, 51, 2492 10.1002/anie.201108663
40. 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 10.1002/anie.201208432
41. Rueping, M.; Tolstoluzhsky, N.; Nikolaienko, P. Chem.-Eur. J. 2013, 19, 14043 10.1002/chem.201302692
42. Yin, F.; Wang, X. S. Org. Lett. 2014, 16, 1128 10.1021/ol403739w
43. Hu, F.; Shao, X.; Zhu, D.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 6105 10.1002/anie.201402573
44. Munavalli, S.; Rohrbaugh, D. K.; Rossman, D. I.; Berg, F. J.; Wagner, G. W.; Durst, H. D. Synth. Commun. 2000, 30, 2847 10.1080/00397910008087435
45. Pluta, R.; Nikolaienko, P.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 1650 10.1002/anie.201307484
46. Honeker, R.; Ernst, J. B.; Glorius, F. Chem.-Eur. J. 2015, 21, 8047 10.1002/chem.201500957
47. Ferry, A.; Billard, T.; Langlois, B.; Bacqu, R. E. J. Org. Chem. 2008, 73, 9362 10.1021/jo8018544
48. Ferry, A.; Billard, T.; Langlois, B. R.; Bacqu, E. Angew. Chem., Int. Ed. 2009, 48, 8551 10.1002/anie.200903387
49. Ferry, A.; Billard, T.; Bacqu, E.; Langlois, B. R. J. Fluorine Chem. 2012, 134, 160 10.1016/j.jfluchem.2011.02.005
50. Baert, F.; Colomb, J.; Billard, T. Angew. Chem., Int. Ed. 2012, 51, 10382 10.1002/anie.201205156
51. Liu, J.; Chu, L.; Qing, F.-L. Org. Lett. 2013, 15, 894 10.1021/ol400032g
52. Yang, Y.-D.; Azuma, A.; Tokunaga, E.; Yamasaki, M.; Shiro, M.; Shibata, N. J. Am. Chem. Soc. 2013, 135, 8782 10.1021/ja402455f
53. Shao, X.; Wang, X.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457 10.1002/anie.201209817
54. Wang, X.; Yang, T.; Cheng, X.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 12860 10.1002/anie.201305075
55. Hu, F.; Shao, X.; Zhu, D.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 6105 10.1002/anie.201402573
56. Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316 10.1002/anie.201403983
57. Wang, Q.; Qi, Z.; Li, X. Adv. Synth. Catal. 2015, 357, 355 10.1002/adsc.201400717
58. Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86 10.1021/jo010579z
59. Godula, K.; Sames, D. Science 2006, 312, 67 10.1126/science.1114731
60. Uto, T.; Shimizu, M.; Ueura, K.; Tsurugi, H.; Satoh, T.; Miura, M. J. Org. Chem. 2008, 73, 298 10.1021/jo7022087
61. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094 10.1002/anie.200806273
62. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792 10.1002/anie.200902996
63. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624 10.1021/cr900005n
64. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677 10.1039/b908581e
65. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215 10.1021/cr100280d
66. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814 10.1021/ar200190g
67. Li, B.-J.; Wang, H.-Y.; Zhu, Q.-L.; Shi, Z.-J. Angew. Chem., Int. Ed. 2012, 51, 3948 10.1002/anie.201200271
68. Song, G.-Y.; Wang, F.; Li, X.-W. Chem. Soc. Rev. 2012, 41, 3651 10.1039/c2cs15281a
69. Inamoto, K.; Arai, Y.; Hiroya, K.; Doi, T. Chem. Commun. 2008, 5529 10.1039/b811362a
70. Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312 10.1002/anie.201102543
71. Smith, L. H. S.; Coote, S. C.; Sneddon, H. F.; Procter, D. J. Angew. Chem., Int. Ed. 2010, 49, 5832 10.1002/anie.201000517
72. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790 10.1021/ja061715q
73. Yang, Y. D.; Azuma, A.; Shibata, N. J. Am. Chem. Soc. 2013, 135, 8782 10.1021/ja402455f
74. Arisawa, M.; Fujimoto, K.; Morinaka, S.; Yamaguchi, M. J. Am. Chem. Soc. 2005, 127, 12226 10.1021/ja0527121
75. Yang, Y.-X.; Hou, W.; Qin, L.-H.; Du, J.-J.; Li, Y.-C. Chem.-Eur. J. 2014, 20, 416 10.1002/chem.201303730
76. Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237 10.1021/ja3092278
77. Xu, C.; Shen, Q. Org. Lett. 2014, 16, 2046 10.1021/ol5006533
78. Yin, W.; Wang, Z.; Huang, Y. Adv. Synth. Catal. 2014, 356, 2998 10.1002/adsc.201400362
79. Xiong, H. Y.; Besset, T. J. Org. Chem. 2015, 80, 4204 10.1021/acs.joc.5b00505
80. Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014, 356, 1443 10.1002/adsc.201400197
81. Jones, W. D.; Feher, F. J. J. Am. Chem. Soc. 1985, 107, 620 10.1021/ja00289a014
82. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066 10.1002/anie.201107334
83. Jones, W. D. Acc. Chem. Res. 2003, 36, 140 10.1021/ar020148i
84. Xu, L.; Cheng, J.; Trudell, M. L. J. Org. Chem. 2003, 68, 5388 10.1021/jo030031n