Oxidative olefination of anilides with unactivated alkenes catalyzed by an (electron-deficient η5-cyclopentadienyl)rhodium(III) complex under ambient conditions

Chemistry - A European Journal

Volumn 21, Issue 25, 2015, Pages 9053-9056

  Takahama, Yuji ^b   Shibata, Yu ^a   Tanaka, Ken ^a,b,c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

alkenes; anilides; C H bond functionalization; olefination; rhodium

Indexed keywords

AMIDES; CHEMICAL REACTIONS; ELECTRONS; OLEFINS; RHODIUM;

AMBIENT CONDITIONS; ANILIDES; C-H BOND CLEAVAGE; C-H BOND FUNCTIONALIZATION; DEUTERIUM KINETIC ISOTOPE EFFECT; ELECTRON-DEFICIENT; OLEFINATION; RHODIUM COMPLEXES;

RHODIUM COMPOUNDS;

EID: 84930667446     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501232     Document Type: Article

References (90)

1. S. De Sarkar, W. Liu, S. I. Kozhushkov, L. Ackermann, Adv. Synth. Catal. 2014, 356, 1461
2. S. I. Kozhushkov, L. Ackermann, Chem. Sci. 2013, 4, 886
3. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651
4. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879
5. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
6. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
7. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
8. J. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170
9. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
10. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212.
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. M. Miura, T. Tsuda, T. Satoh, M. Nomura, Chem. Lett. 1997, 26, 1103
14. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586
15. T. Yokota, M. Tani, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2003, 125, 1476
16. M. Tani, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 1221
17. N. P. Grimster, C. Gauntlett, C. R. A. Godfrey, M. J. Gaunt, Angew. Chem. Int. Ed. 2005, 44, 3125
18. Angew. Chem. 2005, 117, 3185
19. G. Cai, Y. Fu, Y. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 7666
20. A. Maehara, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1159
21. J.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 6452
22. Angew. Chem. 2008, 120, 6552
23. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072
24. J. Wu, X. Cui, L. Chen, G. Jiang, Y. Wu, J. Am. Chem. Soc. 2009, 131, 13888
25. D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315
26. B.-F. Shi, Y.-H. Zhang, J. K. Lam, D.-H. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 460
27. K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2010, 49, 6169
28. Angew. Chem. 2010, 122, 6305
29. K. M. Engle, D.-H. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 14137
30. M. Ye, G.-L. Gao, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 6964
31. D. Leow, G. Li, T.-S. Mei, J.-Q. Yu, Nature 2012, 486, 518
32. G. Li, D. Leow, L. Wan, J.-Q. Yu, Angew. Chem. Int. Ed. 2013, 52, 1245
33. Angew. Chem. 2013, 125, 1283.
34. K. Ueura, T. Satoh, M. Miura, Org. Lett. 2007, 9, 1407
35. N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7094
36. F. Wang, G.-Y. Song, X.-W. Li, Org. Lett. 2010, 12, 5430
37. S. Mochida, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 5776
38. F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9982
39. S. Mochida, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2011, 76, 3024
40. F. W. Patureau, T. Besset, F. Glorius, Angew. Chem. Int. Ed. 2011, 50, 1064
41. Angew. Chem. 2011, 123, 1096
42. S. H. Park, J. Y. Kim, S. Chang, Org. Lett. 2011, 13, 2372
43. J. Willwacher, S. Rakshitb, F. Glorius, Org. Biomol. Chem. 2011, 9, 4736
44. N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449
45. C. Wang, H. Chen, Z. Wang, J. Chen, Y. Huang, Angew. Chem. Int. Ed. 2012, 51, 7242
46. Angew. Chem. 2012, 124, 7354
47. B. Liu, Y. Fan, Y. Gao, C. Sun, C. Xu, J. Zhu, J. Am. Chem. Soc. 2013, 135, 468
48. D. Zhao, C. Nimphius, M. Lindale, F. Glorius, Org. Lett. 2013, 15, 4504
49. B. Li, J. Ma, W. Xie, H. Song, S. Xu, B. Wang, Chem. Eur. J. 2013, 19, 11863.
50. K.-H. Kwon, D. W. Lee, C. S. Yi, Organometallics 2010, 29, 5748
51. T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2011, 13, 706
52. Y. Hashimoto, T. Ueyama, T. Fukutani, K. Hirano, T. Satoh, M. Miura, Chem. Lett. 2011, 40, 1165
53. L. Ackermann, L. Wang, R. Wolfram, A. V. Lygin, Org. Lett. 2012, 14, 728
54. B. Li, J. Ma, N. Wang, H. Feng, S. Xu, B. Wang, Org. Lett. 2012, 14, 736.
55. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254
56. A. García-Rubia, R. G. Arrayas, J. C. Carretero, Angew. Chem. Int. Ed. 2009, 48, 6511
57. Angew. Chem. 2009, 121, 6633
58. X. Zhang, S. Fan, C.-Y. He, X. Wan, Q.-Q. Min, J. Yang, Z.-X. Jiang, J. Am. Chem. Soc. 2010, 132, 4506
59. Y. Lu, D.-H. Wang, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 5916
60. S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2350
61. L. Zheng, J. Wang, Chem. Eur. J. 2012, 18, 9699
62. Y. Donga, G. Liu, Chem. Commun. 2013, 49, 8066
63. W. Liu, X. Yu, C. Kuang, Org. Lett. 2014, 16, 1798
64. L. Yang, G. Zhang, H. Huang, Adv. Synth. Catal. 2014, 356, 1509
65. Y. Lu, H.-W. Wang, J. E. Spangler, K. Chen, P.-P. Cui, Y. Zhao, W.-Y. Sun, J.-Q. Yu, Chem. Sci. 2015, 6, 1923.
66. Y. Zhang, Z. Li, Z.-Q. Liu, Org. Lett. 2012, 14, 226
67. N. Gigant, J.-E. Bäckvall, Org. Lett. 2014, 16, 1664; for that with N-allylphthalimide, see
68. C.-Z. Wu, C.-Y. He, Y. Huang, X. Zhang, Org. Lett. 2013, 15, 5266.
69. N. Gigant, J.-E. Bäckvall, Org. Lett. 2014, 16, 4432.
70. A. Deb, S. Bag, R. Kancherla, D. Maiti, J. Am. Chem. Soc. 2014, 136, 13602.
71. C. S. Sevov, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 10625.
72. A. S. Tsai, M. Brasse, R. G. Bergman, J. A. Ellman, Org. Lett. 2011, 13, 540.
73. X. Li, X. Gong, M. Zhao, G. Song, J. Deng, X. Li, Org. Lett. 2011, 13, 5808.
74. P. Zhao, R. Niu, F. Wang, K. Han, X. Li, Org. Lett. 2012, 14, 4166.
75. III-catalyzed room temperature annulation of aryldiazenecarboxylates with alkenes involving aliphatic ones has been reported; see:, D. Zhao, S. Vásquez-Céspedes, F. Glorius, Angew. Chem. Int. Ed. 2015, 54, 1657
76. Angew. Chem. 2015, 127, 1677.
77. Y. Shibata, K. Tanaka, Angew. Chem. Int. Ed. 2011, 50, 10917
78. Angew. Chem. 2011, 123, 11109
79. Y. Hoshino, Y. Shibata, K. Tanaka, Adv. Synth. Catal. 2014, 356, 1577.
80. 2 using 1; see:, B. Zhou, Y. Yang, H. Tang, J. Du, H. Feng, Y. Li, Org. Lett. 2014, 16, 3900.
81. The oxidative annulation of benzylalcohols with alkynes also proceeds under ambient conditions using 1; see:, M. Fukui, Y. Hoshino, T. Satoh, M. Miura, K. Tanaka, Adv. Synth. Catal. 2014, 356, 1638.
82. K. Morimoto, M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 5359
83. Angew. Chem. 2012, 124, 5455
84. M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura, J. Org. Chem. 2013, 78, 1365
85. H. Baars, Y. Unoh, T. Okada, K. Hirano, T. Satoh, K. Tanaka, C. Bolm, M. Miura, Chem. Lett. 2014, 43, 1782.
86. D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474
87. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326.
88. III-catalyzed vinylation of phenylpyridines and benzamides with vinyl acetate has been reported; see:, K. D. Otley, J. A. Ellman, Org. Lett. 2015, 17, 1332.
89. E. M. Simmons, J. F. Hartwig, Angew. Chem. Int. Ed. 2012, 51, 3066
90. Angew. Chem. 2012, 124, 3120.