Copper-catalyzed aerobic oxidative C-C bond cleavage for C-N bond formation: From ketones to amides

Angewandte Chemie - International Edition

Volumn 53, Issue 25, 2014, Pages 6528-6532

  Tang, Conghui ^a   Jiao, Ning ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

amides; cleavage reactions; copper; ketones; oxygen

Indexed keywords

AMIDES; BIOACTIVITY; CATALYSIS; COPPER; OXYGEN;

ACETOPHENONES; ALKYL SUBSTITUENT; ARYL ALKYL KETONES; BIOLOGICALLY ACTIVE COMPOUNDS; BOND CLEAVAGE REACTION; C-C BOND CLEAVAGES; C-N BOND FORMATIONS; CLEAVAGE REACTION;

KETONES;

ACETOPHENONE; ACETOPHENONE DERIVATIVE; AMIDE; CARBON; COPPER; KETONE; NITROGEN;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ACETOPHENONES; AMIDES; CARBON; CATALYSIS; COPPER; KETONES; MOLECULAR STRUCTURE; NITROGEN; OXIDATION-REDUCTION;

EID: 84902291238     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201403528     Document Type: Article

References (119)

1. For reviews on C-C bond cleavage, see:a) R. H. Crabtree, Chem. Rev. 1985, 85, 245
2. M. Murakami, Y. Ito, Top. Organomet. Chem. 1999, 3, 97
3. B. Rybtchinski, D. Milstein, Angew. Chem. 1999, 111, 918
4. Angew. Chem. Int. Ed. 1999, 38, 870
5. C.-H. Jun, Chem. Soc. Rev. 2004, 33, 610
6. C.-H. Jun, J.-W. Park, Top. Organomet. Chem. 2007, 24, 117
7. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222
8. M. Tobisu, N. Chatani, Chem. Soc. Rev. 2008, 37, 300
9. A. Masarwa, I. Marek, Chem. Eur. J. 2010, 16, 9712
10. M. Murakami, T. Matsuda, Chem. Commun. 2011, 47, 1100.
11. O. G. Kulinkovich, Chem. Rev. 2003, 103, 2597
12. M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117
13. T. Seisera, N. Cramer, Org. Biomol. Chem. 2009, 7, 2835
14. C. A. Carson, M. A. Kerr, Chem. Soc. Rev. 2009, 38, 3051
15. T. Seiser, T. Saget, D. N. Tran, N. Cramer, Angew. Chem. 2011, 123, 7884
16. Angew. Chem. Int. Ed. 2011, 50, 7740
17. T. Seiser, N. Cramer, J. Am. Chem. Soc. 2010, 132, 5340
18. S. C. Bart, P. J. Chirik, J. Am. Chem. Soc. 2003, 125, 886
19. P. A. Wender, A. G. Correa, Y. Sato, R. Sun, J. Am. Chem. Soc. 2000, 122, 7815
20. M. Murakami, H. Amii, K. Shigeto, Y. Ito, J. Am. Chem. Soc. 1996, 118, 8285.
21. J. W. Suggs, C.-H. Jun, J. Am. Chem. Soc. 1984, 106, 3054
22. C.-H. Jun, H. Lee, J. Am. Chem. Soc. 1999, 121, 880
23. M. Gandelman, D. Milstein, Chem. Commun. 2000, 1603
24. C.-H. Jun, D.-Y. Lee, H. Lee, J.-B. Hong, Angew. Chem. 2000, 112, 3214
25. Angew. Chem. Int. Ed. 2000, 39, 3070
26. A. M. Dreis, C. J. Douglas, J. Am. Chem. Soc. 2009, 131, 412
27. N. Chatani, Y. Ie, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 1999, 121, 8645
28. J. Wang, W. Chen, S. Zuo, L. Liu, X. Zhang, J. Wang, Angew. Chem. 2012, 124, 12500
29. Angew. Chem. Int. Ed. 2012, 51, 12334
30. F. D. Lewis, J. G. Magyar, J. Org. Chem. 1972, 37, 2102
31. N. Zhang, J. Vozzolo, J. Org. Chem. 2002, 67, 1703
32. Z.-Q. Lei, H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, J. Sun, Z.-J. Shi, Angew. Chem. 2012, 124, 2744
33. Angew. Chem. Int. Ed. 2012, 51, 2690.
34. For reviews on aerobic oxidative reactions, see:a) S. S. Stahl, Angew. Chem. 2004, 116, 3480
35. Angew. Chem. Int. Ed. 2004, 43, 3400
36. B. M. Stoltz, Chem. Lett. 2004, 33, 362
37. T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329
38. K. M. Gligorich, M. S. Sigman, Angew. Chem. 2006, 118, 6764
39. Angew. Chem. Int. Ed. 2006, 45, 6612
40. M. S. Sigman, D. R. Jensen, Acc. Chem. Res. 2006, 39, 221
41. J. Muzart, Chem. Asian J. 2006, 1, 508
42. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318
43. J. Piera, J. E. Bäckvall, Angew. Chem. 2008, 120, 3558
44. Angew. Chem. Int. Ed. 2008, 47, 3506
45. S. S. Stahl, Science 2005, 309, 1824
46. M. J. Schultz, M. S. Sigman, Tetrahedron 2006, 62, 8227
47. W. Wu, H. Jiang, Acc. Chem. Res. 2012, 45, 1736
48. Z. Shi, C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3381
49. A. N. Campbell, S. S. Stahl, Acc. Chem. Res. 2012, 45, 851.
50. For examples of aerobic oxidative C=C and C≡C bond cleavage reactions, see:a) T. Wang, N. Jiao, J. Am. Chem. Soc. 2013, 135, 11692
51. R. Lin, F. Chen, N. Jiao, Org. Lett. 2012, 14, 4158
52. M. Tokunaga, Y. Shirogane, H. Aoyama, Y. Obora, Y. Tsuji, J. Organomet. Chem. 2005, 690, 5378
53. Y. Hayashi, M. Takeda, Y. Miyamoto, M. Shoji, Chem. Lett. 2002, 414
54. C.-X. Miao, B. Yu, L.-N. He, Green Chem. 2011, 13, 541
55. S.-i. Hirashima, Y. Kudo, T. Nobuta, N. Tada, A. Itoh, Tetrahedron Lett. 2009, 50, 4328
56. T. Yamaguchi, T. Nobuta, Y. Kudo, S.-i. Hirashima, N. Tada, T. Miura, A. Itoh, Synlett 2013, 607
57. A. Wang, H. Jiang, J. Am. Chem. Soc. 2008, 130, 5030
58. Y. Liu, F. Song, S. Guo, J. Am. Chem. Soc. 2006, 128, 11332
59. A. Das, R. Chaudhuri, R.-S. Liu, Chem. Commun. 2009, 4046.
60. For examples of aerobic oxidative decarboxylation or decarbonylation reactions, see:a) C. Zhang, Z. Xu, T. Shen, G. Wu, L. Zhang, N. Jiao, Org. Lett. 2012, 14, 2362
61. B. Tiwari, J. Zhang, Y. R. Chi, Angew. Chem. 2012, 124, 1947
62. Angew. Chem. Int. Ed. 2012, 51, 1911
63. Q. Feng, Q. Song, J. Org. Chem. 2014, 79, 1867
64. Q. Song, Q. Feng, K. Yang, Org. Lett. 2014, 16, 624
65. J. Liu, Q. Liu, H. Yi, C. Qin, R. Bai, X. Qi, Y. Lan, A. Lei, Angew. Chem. 2014, 126, 512
66. Angew. Chem. Int. Ed. 2014, 53, 502
67. B. Wen, Y. Li, C. Chen, W. Ma, J. Zhao, Chem. Eur. J. 2010, 16, 11859.
68. H. Liu, C. Dong, Z. Zhang, P. Wu, X. Jiang, Angew. Chem. 2012, 124, 12738
69. Angew. Chem. Int. Ed. 2012, 51, 12570.
70. L. Zhang, X. Bi, X. Guan, X. Li, Q. Liu, B.-D. Barry, P. Liao, Angew. Chem. 2013, 125, 11513
71. Angew. Chem. Int. Ed. 2013, 52, 11303.
72. For recently reported examples of copper-catalyzed C-C bond cleavage reactions, see:a) T. Sugiishi, A. Kimura, H. Nakamura, J. Am. Chem. Soc. 2010, 132, 5332
73. C. He, S. Guo, L. Huang, A. Lei, J. Am. Chem. Soc. 2010, 132, 8273
74. S. Chiba, L. Zhang, G. Y. Ang, B. W.-Q. Hui, Org. Lett. 2010, 12, 2052
75. M. Sai, H. Yorimitsu, K. Oshima, Angew. Chem. 2011, 123, 3352
76. Angew. Chem. Int. Ed. 2011, 50, 3294
77. F. Chen, C. Qin, Y. Cui, N. Jiao, Angew. Chem. 2011, 123, 11689
78. Angew. Chem. Int. Ed. 2011, 50, 11487
79. W. Zhou, Y. Yang, Y. Liu, G.-J. Deng, Green Chem. 2013, 15, 76.
80. For previous reports on the C(CO)-C(α) bond cleavage of ketones to give amides, see:a) J. Y. Becker, L. L. Miller, T. M. Siege, J. Am. Chem. Soc. 1975, 97, 849
81. K. Ishihara, T. Yano, Org. Lett. 2004, 6, 1983
82. Y. Kuninobu, T. Uesugi, A. Kawata, K. Takai, Angew. Chem. 2011, 123, 10590
83. Angew. Chem. Int. Ed. 2011, 50, 10406.
84. For recent examples of copper-catalyzed aerobic oxidative reactions, see:a) S. Chiba, L. Zhang, J.-Y. Lee, J. Am. Chem. Soc. 2010, 132, 7266
85. H. Wang, Y. Wang, D. Liang, L. Liu, J. Zhang, Q. Zhu, Angew. Chem. 2011, 123, 5796
86. Angew. Chem. Int. Ed. 2011, 50, 5678
87. Q. Liu, P. Wu, Y. Yang, Z. Zeng, J. Liu, H. Yi, A. Lei, Angew. Chem. 2012, 124, 4744
88. Angew. Chem. Int. Ed. 2012, 51, 4666
89. L. Zhang, G. Y. Ang, S. Chiba, Org. Lett. 2011, 13, 1622
90. C. Zhang, Z. Xu, L. Zhang, N. Jiao, Angew. Chem. 2011, 123, 11284
91. Angew. Chem. Int. Ed. 2011, 50, 11088; for mechanistic studies, see
92. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068
93. Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 14654
94. N. Decharin, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 5732
95. E. Boess, D. Sureshkumar, A. Sud, C. Wirtz, C. Fares, M. Klussmann, J. Am. Chem. Soc. 2011, 133, 8106
96. K. Schröder, B. Join, A. J. Amali, K. Junge, X. Ribas, M. Costas, M. Beller, Angew. Chem. 2011, 123, 1461
97. Angew. Chem. Int. Ed. 2011, 50, 1425.
98. C. Tang, N. Jiao, J. Am. Chem. Soc. 2012, 134, 18924
99. W. Zhou, L. Zhang, N. Jiao, Angew. Chem. 2009, 121, 7228
100. Angew. Chem. Int. Ed. 2009, 48, 7094
101. C. Qin, T. Shen, C. Tang, N. Jiao, Angew. Chem. 2012, 124, 7077
102. Angew. Chem. Int. Ed. 2012, 51, 6971
103. C. Tang, Y. Yuan, Y. Cui, N. Jiao, Eur. J. Org. Chem. 2013, 7480
104. T. Shen, T. Wang, C. Qin, N. Jiao, Angew. Chem. 2013, 125, 6809
105. Angew. Chem. Int. Ed. 2013, 52, 6677
106. F. Chen, X. Huang, Y. Cui, N. Jiao, Chem. Eur. J. 2013, 19, 11199
107. Y. Yuan, T. Shen, K. Wang, N. Jiao, Chem. Asian J. 2013, 8, 2932.
108. W. Zhu, D. Ma, Chem. Commun. 2004, 888
109. J. Andersen, U. Madsen, F. Björkling, X. Liang, Synlett 2005, 2209.
110. K. F. Z. Schmidt, Angew. Chem. 1923, 36, 511
111. S. Lang, J. A. Murphy, Chem. Soc. Rev. 2006, 35, 146.
112. C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev. 2012, 41, 3464
113. M. Gõmez-Gallego, M. A. Sierra, Chem. Rev. 2011, 111, 4857.
114. H. R. Lucas, L. Li, A. A. N. Sarjeant, M. A. Vance, E. I. Solomon, K. D. Karlin, J. Am. Chem. Soc. 2009, 131, 3230
115. C. Wurtele, O. Sander, V. Lutz, T. Waitz, F. Tuczek, S. Schindler, J. Am. Chem. Soc. 2009, 131, 7544
116. I. Garcia-Bosch, A. Company, J. R. Frisch, M. Torrent-Sucarrat, M. Cardellach, I. Gamaba, M. Guell, L. Casella, L. Que, Jr., X. Ribas, J. M. Luis, M. Costas, Angew. Chem. 2010, 122, 2456
117. Angew. Chem. Int. Ed. 2010, 49, 2406.
118. When 1-phenylhexan-1-one was used as the substrate, pentanal was detected as a side product by mass spectrometry; the mass spectrum was carefully compared with standard MS spectra from http://webbook.nist.gov/chemistry. For C(CO)-C(alkyl) bond cleavage reactions of ketones with an alkyl fragment leaving as a carbonyl moiety, see
119. H. S. Fung, B. Z. Li, K. S. Chan, Organometallics 2012, 31, 570.