Synthesis of indoles through Rh(III)-catalyzed C-H cross-coupling with allyl carbonates

Tetrahedron Letters

Volumn 55, Issue 11, 2014, Pages 1859-1862

  Gong, Tian Jun ^a   Cheng, Wan Min ^a   Su, Wei ^a   Xiao, Bin ^a   Fu, Yao ^a  

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

Author keywords

C H activation; Indoles; Rh(III) catalyzed

Indexed keywords

1 (2 METHYL 1H INDOL 1 YL)ETHANONE; 1 (5 METHOXY 2 METHYL 1H INDOL 1 YL)ETHANONE; 1 (5 TRIFLUOROMETHYL 2 METHYL 1H INDOL 1 YL)ETHANONE; 1 [5 (6 CHLOROHEXYLOXY) 2 METHYL 1H INDOL 1 YL]ETHANONE; 1 ACETYL 2 METHYL 1 INDOL 5 YL PIVALATE; 1 ACETYL 2 METHYL 1H INDOL 5 YL ACETATE; 2 (1 ACETYL 2 METHYL 1H INDOL 5 YL)ETHYL 4 METHYLBENZENESULFONATE; CARBONIC ACID DERIVATIVE; DIETHYL (1 ACETYL 2 METHYL 1H INDOL 5 YLL)METHYLPHOSPHONATE; INDOLE DERIVATIVE; INDOMETACIN; METHYL 2 ACETAMIDO 3 (1 ACETYL 2 METHYL 1H INDOL 5 YL)PROPANOATE; PRAVADOLINE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84896732303     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.11.065     Document Type: Article

References (41)

1. A.J. Kochanowska-Karamyan, and M.T. Hamann Chem. Rev. 110 2010 4489
2. M. Bandini, and A. Eichholzer Angew. Chem.; Int. Ed. 48 2009 9608
3. M. Arisawa, Y. Kasaya, T. Obata, T. Sasaki, T. Nakamura, T. Araki, K. Yamamoto, A. Sasaki, A. Yamano, M. Ito, H. Abe, Y. Ito, and S. Shuto J. Med. Chem. 55 2012 8152
4. S. Cacchi, and G. Fabrizi Chem. Rev. 105 2005 2873
5. G.R. Humphrey, and J.T. Kuethe Chem. Rev. 106 2006 2875
6. X. Cui, J. Li, Y. Fu, L. Liu, and Q.-X. Guo Tetrahedron Lett. 49 2008 3458
7. M. Inman, and C. Moody J. Chem. Sci. 4 2013 29
8. For Pd-catalyzed direct C-H indoles synthesis, see: Y. Tan, and J.F. Hartwig J. Am. Chem. Soc. 132 2010 3676
9. J.J. Neumann, S. Rakshit, T. Dröge, S. Würtz, and F. Glorius Chem. Eur. J. 17 2011 7298
10. Y. Wei, I. Deb, and N. Yoshikai J. Am. Chem. Soc. 134 2012 9098
11. For Rh-catalyzed direct C-H indoles synthesis, see: D.R. Stuart, M. Bertrand-Laperle, K.M.N. Burgess, and K. Fagnou J. Am. Chem. Soc. 130 2008 16474
12. D.R. Stuart, P. Alsabeh, M. Kuhn, and K. Fagnou J. Am. Chem. Soc. 132 2010 18326
13. M.P. Huestis, L. Chan, D.R. Stuart, and K. Fagnou Angew. Chem.; Int. Ed. 50 2011 1338
14. C. Wang, H. Sun, Y. Fang, and Y. Huang Angew. Chem.; Int. Ed. 52 2013 5795
15. For Cu-catalyzed direct C-H indoles synthesis, for see: R. Bernini, G. Fabrizi, A. Sferrazza, and S. Cacchi Angew. Chem.; Int. Ed. 48 2009 8078 8081
16. Y.-M. Li, M. Sun, H.-L. Wang, Q.-P. Tian, and S.-D. Yang Angew. Chem.; Int. Ed. 52 2013 3972
17. For Ru-catalyzed direct C-H indoles synthesis, see: L. Ackermann, and A.V. Lygin Org. Lett. 15 2013 3670
18. For Fe-catalyzed direct C-H indoles synthesis, see: Z.-H. Guan, Z.-Y. Yan, Z.-H. Ren, X.-Y. Liu, and Y.-M. Liang Chem. Commun. 2010 2823
19. For Au-catalyzed direct C-H indoles synthesis, see: Y. Wang, L. Ye, and L. Zhang Chem. Commun. 2011 7815
20. For Ni-catalyzed direct C-H indoles synthesis, see: W. Song, and L. Ackermann Chem. Commun. 2013 6638
21. For Rh(III)-catalyzed direct C-H allylation of arenes with allylic carbonates, see: H. Wang, N. Schröder, and F. Glorius Angew. Chem.; Int. Ed. 52 2013 5386
22. C. Feng, D. Feng, and T.-P. Loh Org. Lett. 14 2012 764
23. During the preparation of our manuscript, we noted a similar study has been published: A. Cajaraville, S. López, J.A. Varela, and C. Saá Org. Lett. 15 2013 4576
24. T. Satoh, and M. Miura Chem. Eur. J. 16 2010 11212
25. D.A. Colby, A.S. Tsai, R.G. Bergman, and J.A. Ellman Acc. Chem. Res. 45 2012 814
26. G. Song, F. Wang, and X. Li Chem. Soc. Rev. 41 2012 3651
27. P. Anbarasan, H. Neumann, and M. Beller Angew. Chem.; Int. Ed. 50 2011 519
28. T.-J. Gong, B. Xiao, W.-M. Cheng, W. Su, J. Xu, Z.-J. Liu, L. Liu, and Y. Fu J. Am. Chem. Soc. 135 2013 10630
29. E. Angelini, C. Balsamini, F. Bartoccini, S. Lucarini, and G. Piersanti J. Org. Chem. 73 2008 5654
30. Y. Lian, and H.M.L. Davies J. Am. Chem. Soc. 132 2010 440
31. F.O. Arp, and G.C. Fu J. Am. Chem. Soc. 128 2006 14264
32. B.A. Haag, Z.-G. Zhang, J.-S. Li, and P. Knochel Angew. Chem.; Int. Ed. 49 2010 9513
33. M.R. Bell, T.E. D'Ambra, V. Kumar, M.A. Eissenstat, J.L. Herrmann, J.R. Wetzel, D. Rosi, R.E. Philion, S.J. Daum, D.J. Hlasta, R.K. Kullnig, H.J. Ackerman, D.R. Haubrich, D.A. Luttinger, E.R. Baizman, M.S. Miller, and S.J. Ward J. Med. Chem. 34 1991 1099
34. E.M. Simmons, and J.F. Hartwig Angew. Chem.; Int. Ed. 51 2012 3066
35. L. Li, W.W. Brennessel, and W.D. Jones J. Am. Chem. Soc. 130 2008 12414
36. B. Xiao, T.-J. Gong, J. Xu, Z.-J. Liu, and L. Liu J. Am. Chem. Soc. 133 2011 1466
37. T.-J. Gong, B. Xiao, Z.-J. Liu, J. Wan, J. Xu, D.-F. Luo, Y. Fu, and L. Liu Org. Lett. 13 2011 3235
38. M. Brasse, J. Cámpora, J.A. Ellman, and R.G. Bergman J. Am. Chem. Soc. 135 2013 6427
39. K.-T. Yip, and D. Yang Chem. Asian J. 6 2011 2166
40. J.D. Weaver, A. Recio III, A.J. Grenning, and J.A. Tunge Chem. Rev. 111 2011 1846
41. R. Shang, and L. Liu Sci. China Chem. 54 2011 1670