An efficient rhodium/oxygen catalytic system for oxidative heck reaction of indoles and alkenes via C-H functionalization

Advanced Synthesis and Catalysis

Volumn 356, Issue 7, 2014, Pages 1509-1515

  Yang, Lei ^a   Zhang, Guoying ^a   Huang, Hanmin ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

alkenes; indoles; molecular oxygen; oxidative Heck reaction; rhodium

Indexed keywords

EID: 84900499111     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201301107     Document Type: Article

References (85)

1. R. Rossi, F. Bellina, M. Lessi, Synthesis 2010, 4131
2. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
3. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780
4. W. Shi, C. Liu, A. Lei, Chem. Soc. Rev. 2011, 40, 2761
5. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
6. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. 2012, 124, 10382
7. Angew. Chem. Int. Ed. 2012, 51, 10236
8. B.-J. Li, Z.-J. Shi, Chem. Soc. Rev. 2012, 41, 5588
9. L. Yang, H. Huang, Catal. Sci. Technol. 2012, 2, 1099
10. B. Li, P. H. Dixneuf, Chem. Soc. Rev. 2013, 42, 5744.
11. I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119
12. Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166
13. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992
14. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633.
15. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731
16. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
17. Angew. Chem. Int. Ed. 2009, 48, 5094
18. J. L. Bras, J. Muzart, Chem. Rev. 2011, 111, 1170.
19. L. Ackermann, Chem. Rev. 2011, 111, 1315
20. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879
21. S. I. Kozhushkov, L. Ackermann, Chem. Sci. 2013, 4, 886.
22. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
23. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212
24. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
25. F. W. Patureau, J. Wencel-Delord, F. Glorius, Aldrichimica Acta 2012, 45, 31.
26. S. S. Stahl, Angew. Chem. 2004, 116, 3480
27. Angew. Chem. Int. Ed. 2004, 43, 3400
28. T. Punniyamurthy, S. Velusamy, J. Iq, Chem. Rev. 2005, 105, 2329
29. J. Piera, J. E. Bäckvall, Angew. Chem. 2008, 120, 3558
30. Angew. Chem. Int. Ed. 2008, 47, 3506
31. K. M. Gligorich, M. S. Sigman, Chem. Commun. 2009, 3854
32. A. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851
33. W. Wu, H. Jiang, Acc. Chem. Res. 2012, 45, 1736
34. Z. Shi, C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381.
35. R. J. Sundberg, Indoles, Academic Press, San Diego, 1996
36. M. Somei, F. Yamada, Nat. Prod. Rep. 2005, 22, 73
37. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786
38. Angew. Chem. Int. Ed. 2009, 48, 9608
39. T. Lemster, U. Pindur, G. Lenglet, S. Depauw, C. Dassi, M.-H. David-Cordonnier, Eur. J. Med. Chem. 2009, 44, 3235
40. A. J. Kochanowska-Karamyan, M. T. Hamann, Chem. Rev. 2010, 110, 4489
41. A. W. Schmidt, K. R. Reddy, H.-J. Knölker, Chem. Rev. 2012, 112, 3193
42. M. Shiri, Chem. Rev. 2012, 112, 3508
43. G. S. Singh, Z. Y. Desta, Chem. Rev. 2012, 112, 6104.
44. E. Capito, J. M. Brown, A. Ricci, Chem. Commun. 2005, 1854
45. N. P. Grimster, C. Gauntlett, C. R. A. Godfrey, M. J. Gaunt, Angew. Chem. 2005, 117, 3185
46. Angew. Chem. Int. Ed. 2005, 44, 3125
47. A. Maehara, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1159
48. A. García-Rubia, R. Gõmez Arrayás, J. C. Carretero, Angew. Chem. 2009, 121, 6633
49. Angew. Chem. Int. Ed. 2009, 48, 6511
50. A. García-Rubia, B. Urones, R. Gõmez Arrayás, J. C. Carretero, Chem. Eur. J. 2010, 16, 9676; for one isolated example of Ru(II)/Cu system-catalyzed alkenylation of 1-methylindole-3-carboxylic acid, see
51. T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2011, 13, 706; for one isolated example of Rh(III)/Ag/Cu system-catalyzed alkenylation of acetylindole, see
52. F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982.
53. V. Lanke, K. R. Prabhu, Org. Lett. 2013, 15, 2818
54. B. Li, J. Ma, W. Xie, H. Song, S. Xu, B. Wang, Chem. Eur. J. 2013, 19, 11863.
55. Y. Nakao, K. S. Kanyiva, S. Oda, T. Hiyama, J. Am. Chem. Soc. 2006, 128, 8146
56. D. J. Schipper, M. Hutchinson, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6910
57. L. L. Suarez, M. F. Greaney, Chem. Commun. 2011, 47, 7992
58. Z. Ding, N. Yoshikai, Angew. Chem. 2012, 124, 4776
59. Angew. Chem. Int. Ed. 2012, 51, 4698.
60. G. Zhang, L. Yang, Y. Wang, Y. Xie, H. Huang, J. Am. Chem. Soc. 2013, 135, 8850; for Ru(II)-catalyzed aerobic alkenylation, see
61. K. Graczyk, W. Ma, L. Ackermann, Org. Lett. 2012, 14, 4110; for examples of some Rh(III)-catalyzed aerobic oxidative couplings, see
62. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407
63. K. Ueura, T. Satoh, M. Miura, J. Org. Chem. 2007, 72, 5362
64. M. Shimizu, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 3478
65. T. Fukutani, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 5198
66. K. Morimoto, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2068
67. T. Fukutani, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 2867.
68. B. Qian, S. Guo, J. Shao, Q. Zhu, L. Yang, C. Xia, H. Huang, J. Am. Chem. Soc. 2010, 132, 3650
69. S. Guo, B. Qian, Y. Xie, C. Xia, H. Huang, Org. Lett. 2011, 13, 522
70. P. Xie, Y. Xie, B. Qian, H. Zhou, C. Xia, H. Huang, J. Am. Chem. Soc. 2012, 134, 9902
71. L. Yang, B. Qian, H. Huang, Chem. Eur. J. 2012, 18, 9511.
72. L. Yang, Q. Zhu, S. Guo, B. Qian, C. Xia, H. Huang, Chem. Eur. J. 2010, 16, 1638
73. Y. Xie, Y. Zhao, B. Qian, L. Yang, C. Xia, H. Huang, Angew. Chem. 2011, 123, 5800
74. Angew. Chem. Int. Ed. 2011, 50, 5682.
75. L. Ackermann, A. V. Lygin, Org. Lett. 2011, 13, 3332
76. J. Shi, B. Zhou, Y. Yang, Y. Li, Org. Biomol. Chem. 2012, 10, 8953.
77. E. M. Beck, N. P. Grimster, R. Hatley, M. J. Gaunt, J. Am. Chem. Soc. 2006, 128, 2528
78. M. Zhang, H. Neumann, M. Beller, Angew. Chem. 2013, 125, 625
79. Angew. Chem. Int. Ed. 2013, 52, 597
80. S. Michlik, R. Kempe, Nat. Chem. 2013, 5, 140
81. Z. Shi, M. Suri, F. Glorius, Angew. Chem. 2013, 125, 4992
82. Angew. Chem. Int. Ed. 2013, 52, 4892.
83. CCDC 949387 (A) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
84. L. S. Santos, Reactive Intermediates: MS Investigations in Solution, Wiley-VCH, Weinheim, Germany, 2010.
85. During the revision process of our manuscript, an example of C-2 alkenylation of N-pyrimidylindoles catalyzed by Rh(III)/Cu catalytic system was reported. However, in this paper, only acrylates were used as the substrate, see:, B. Gong, J. Shi, X. Wang, Y. Yan, Q. Li, Y. Meng, H. E. Xu, W. Yi, Adv. Synth. Catal. 2014, 356, 137.