Copper-catalyzed aerobic oxidative coupling of aryl acetaldehydes with anilines leading to α-ketoamides

Angewandte Chemie - International Edition

Volumn 50, Issue 47, 2011, Pages 11088-11092

  Zhang, Chun ^a   Xu, Zejun ^a   Zhang, Liangren ^a   Jiao, Ning ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

amides; copper; cross coupling; oxidation; oxygen

Indexed keywords

BIOLOGICALLY ACTIVE COMPOUNDS; CROSS-COUPLINGS; DIOXYGEN ACTIVATION; KETOAMIDES; OXIDATIVE COUPLINGS; STRUCTURAL UNIT;

ALDEHYDES; AMIDES; ANILINE; BIOACTIVITY; COPPER; ORGANIC COMPOUNDS; OXIDATION; OXYGEN;

MOLECULAR OXYGEN;

ACETALDEHYDE; AMIDE; ANILINE; ANILINE DERIVATIVE; COPPER; KETONE;

AEROBIC METABOLISM; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ACETALDEHYDE; AEROBIOSIS; AMIDES; ANILINE COMPOUNDS; CATALYSIS; COPPER; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 81255190874     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105285     Document Type: Article

References (106)

1. H. Knust, M. Nettekoven, E. Pinard, O. Roche, M. Rogers-Evans, PCT Int. Appl. WO 2009016087, 2009
2. C. A. Crowley, N. G. J. Delaet, J. Ernst, C. G. Grove, B. Hepburn, B. King, C. J. Larson, S. Miller, K. Pryor, L. J. Shuster, PCT Int. Appl. WO 2007146712, 2007
3. S. Úlvarez, R. Úlvarez, H. Khanwalkar, P. Germain, G. Lemaire, F. Rodríguez-Barrios, H. Gronemeyer, A. R. de Lera, Bioorg. Med. Chem. 2009, 17, 4345
4. D. V. Patel, R. D. J. Gless, H. Webb, K. Heather, S. K. Anandan, B. R. Aavula, PCT Int. Appl. WO 2008073623, 2008.
5. J. L. Jesuraj, J. Sivaguru, Chem. Commun. 2010, 46, 4791
6. Z. Zhang, Q. Zhang, Z. Ni, Q. Liu, Chem. Commun. 2010, 46, 1269
7. K. K. S. Sai, P. M. Esteves, E. T. da Penha, D. A. Klumpp, J. Org. Chem. 2008, 73, 6506
8. D. Tomita, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 6946
9. L. Yang, D.-X. Wang, Z.-T. Huang, M.-X. Wang, J. Am. Chem. Soc. 2009, 131, 10390.
10. A. Chiou, T. Markidis, V. C. Kokotou, R. Verger, G. Kokotus, Org. Lett. 2000, 2, 347
11. G. M. Dubowchik, J. L. Ditta, J. J. Herbst, S. Bollini, A. Vinitsky, Bioorg. Med. Chem. Lett. 2000, 10, 559
12. G. M. Dubowchik, V. M. Vrudhula, B. Dasgupta, J. Ditta, T. Chen, S. Sheriff, K. Sipman, M. Witmer, J. Tredup, D. M. Vyas, T. A. Verdoorn, S. Bollini, A. Vinitsky, Org. Lett. 2001, 3, 3987
13. R. P. Singh, J. M. Shreeve, J. Org. Chem. 2003, 68, 6063.
14. J. E. Semple, T. D. Owens, K. Nguyen, O. E. Levy, Org. Lett. 2000, 2, 2769
15. L. Banfi, G. Guanti, R. Riva, Chem. Commun. 2000, 985
16. M. Nakamura, J. Inoue, T. Yamada, Bioorg. Med. Chem. Lett. 2000, 10, 2807
17. A. Papanikos, J. Rademann, M. Medal, J. Am. Chem. Soc. 2001, 123, 2176
18. J. Chen, X. Chen, M. Bois-Choussy, J. Zhu, J. Am. Chem. Soc. 2006, 128, 87
19. L. El Kaïm, R. Gamez-Montano, L. Grimaud, T. Ibarra-Rivera, Chem. Commun. 2008, 1350.
20. J. Liu, R. Zhang, S. Wang, W. Sun, C. Xia, Org. Lett. 2009, 11, 1321
21. E. R. Murphy, J. R. Martinelli, N. Zaborenko, S. L. Buchwald, K. F. Jensen, Angew. Chem. 2007, 119, 1764
22. Angew. Chem. Int. Ed. 2007, 46, 1734
23. T. Fukuyama, S. Nishitani, T. Inouye, K. Morimoto, I. Ryu, Org. Lett. 2006, 8, 1383
24. M. Iizuka, Y. Kondo, Chem. Commun. 2006, 1739.
25. J.-M. Grassot, G. Masson, J. Zhu, Angew. Chem. 2008, 120, 961
26. Angew. Chem. Int. Ed. 2008, 47, 947
27. M. Bouma, G. Masson, J. Zhu, J. Org. Chem. 2010, 75, 2748
28. D. Coffinier, L. E. Kaim, L. Grimaud, Org. Lett. 2009, 11, 1825
29. R. Mossetti, T. Pirali, G. C. Tron, J. Zhu, Org. Lett. 2010, 12, 820
30. Q. Liu, S. Perreault, T. Rovis, J. Am. Chem. Soc. 2008, 130, 14066
31. Z. F. Al-Rashid, W. L. Johnson, R. P. Hsung, Y. Wei, P.-Y. Yao, R. Liu, K. Zhao, J. Org. Chem. 2008, 73, 8780
32. B. Song, S. Wang, C. Sun, H. Deng, B. Xu, Tetrahedron Lett. 2007, 48, 8982.
33. Dioxygen has been used as an ideal oxidant, for some reviews, see: T. Punniyamurthy, S. Velusamy, J. Iqbal, Chem. Rev. 2005, 105, 2329
34. S. S. Stahl, Angew. Chem. 2004, 116, 3480
35. Angew. Chem. Int. Ed. 2004, 43, 3400
36. M. S. Sigman, D. R. Jensen, Acc. Chem. Res. 2006, 39, 221
37. J. Piera, J.-E. Bäckvall, Angew. Chem. 2008, 120, 3558
38. Angew. Chem. Int. Ed. 2008, 47, 3506
39. K. M. Gligorich, M. S. Sigman, Chem. Commun. 2009, 3854
40. B. M. Stoltz, Chem. Lett. 2004, 33, 362.
41. C. Zhang, N. Jiao, J. Am. Chem. Soc. 2010, 132, 28.
42. For some reviews on C-H bond activation in the last two years, see: C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677
43. G. E. Dobereiner, R. H. Crabtree, Chem. Rev. 2010, 110, 681
44. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
45. C. Copéret, Chem. Rev. 2010, 110, 656
46. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
47. I. A. I. Mkhalid, J. H. Barnard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 110, 890
48. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704
49. A. Gunay, K. H. Theopold, Chem. Rev. 2010, 110, 1060
50. D. Balcells, E. Colt, O. Eisenstein, Chem. Rev. 2010, 110, 749
51. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082
52. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293
53. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
54. J. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170
55. L. Ackermann, Chem. Rev. 2011, 111, 1315.
56. For reviews, see: E. I. Solomon, P. Chen, M. Metz, S.-K. Lee, A. E. Palmer, Angew. Chem. 2001, 113, 4702
57. Angew. Chem. Int. Ed. 2001, 40, 4570
58. E. I. Solomon, U. M. Sundaram, T. E. Machonkin, Chem. Rev. 1996, 96, 2563.
59. For some copper-catalyzed reactions involving dioxygen activation in recent years, see: S. Chiba, L. Zhang, J.-Y. Lee, J. Am. Chem. Soc. 2010, 132, 7266
60. H. Wang, Y. Wang, D. Liang, L. Liu, J. Zhang, Q. Zhu, Angew. Chem. 2011, 123, 5796
61. Angew. Chem. Int. Ed. 2011, 50, 5678
62. S. Chiba, L. Zhang, G. Y. Ang, B. W.-Q. Hui, Org. Lett. 2010, 12, 2052
63. J. Wang, J. Wang, Y. Zhu, P. Lu, Y. Wang, Chem, Chem. Commun. 2011, 47, 3275
64. L. Zhang, G. Y. Ang, S. Chiba, Org. Lett. 2011, 13, 1622
65. A. Häusser, M. Trautmann, E. Roduner, Chem. Commun. 2011, 47, 6954
66. C. Würtele, O. Sander, V. Lutz, T. Waitz, F. Tuczek, S. Schindler, J. Am. Chem. Soc. 2009, 131, 7544
67. H. R. Lucas, L. Li, A. A. Narducci Sarjeant, M. A. Vance, E. I. Salomon, K. D. Karlin, J. Am. Chem. Soc. 2009, 131, 3230
68. I. Garcia-Bosch, A. Company, J. R. Frisch, M. Torrent-Sucarrat, M. Cardellach, I. Gamba, M. Güell, L. Casella, L. Que, Jr., X. Ribas, J. M. Luis, M. Costas, Angew. Chem. 2010, 122, 2456
69. Angew. Chem. Int. Ed. 2010, 49, 2406
70. S. Palavicini, A. Granata, E. Monzani, L. Casella, J. Am. Chem. Soc. 2005, 127, 18031; for mechanistic studies, see
71. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068
72. A. E. King, T. C. Brunold, S. S. Stahl, J. Am. Chem. Soc. 2009, 131, 5044
73. Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 14654
74. N. Decharin, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 5732
75. A. N. Campbell, P. B. White, L. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 15116
76. Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522
77. E. Boess, D. Sureshkumar, A. Sud, C. Wirtz, C. Fares, M. Klussmann, J. Am. Chem. Soc. 2011, 133, 8106
78. P. Chen, E. I. Solomon, J. Am. Chem. Soc. 2004, 126, 4991
79. M. P. Lanci, V. V. Simirnov, C. J. Cramer, E. V. Gauchenova, J. Sundermeyer, J. P. Roth, J. Am. Chem. Soc. 2007, 129, 14697
80. M. Rolff, J. Schottenheim, G. Peters, F. Tuczek, Angew. Chem. 2010, 122, 6583
81. Angew. Chem. Int. Ed. 2010, 49, 6438
82. K. Schröder, B. Join, A. J. Amali, K. Junge, X. Ribas, M. Costas, M. Beller, Angew. Chem. 2011, 123, 1461
83. Angew. Chem. Int. Ed. 2011, 50, 1425.
84. C. Zhang, N. Jiao, Angew. Chem. 2010, 122, 6310
85. Angew. Chem. Int. Ed. 2010, 49, 6174.
86. A. Rieche, E. Hoeft, H. Schultze, Chem. Ber. 1964, 97, 195
87. Science of Synthesis. Compounds with One Saturated Carbon-Heteroatom Bond. Peroxides, Vol. 38 (Ed.:, A. Berkessel,), Thieme, Stuttgart, 2009, pp. 9-141
88. A. G. Davies, R. V. Foster, R. Nery, J. Chem. Soc. 1954, 2204
89. H. Yamamoto, M. Akutagawa, H. Aoyama, Y. Omote, J. Chem. Soc. Perkin Trans. 1 1980, 2300
90. H. Nakamura, T. Goto, Bull. Chem. Soc. Jpn. 1988, 61, 3776.
91. H. V. Obias, Y. Lin, N. N. Murthy, E. Pidcock, E. I. Solomon, M. Ralle, N. J. Blackburn, Y.-M. Neuhold, A. D. Zuberbühler, K. D. Karlin, J. Am. Chem. Soc. 1998, 120, 12960
92. V. Mahadevan, M. J. Henson, E. I. Solomon, T. D. P. Stack, J. Am. Chem. Soc. 2000, 122, 10249
93. A. Kunishita, H. Ishimaru, S. Nakashima, T. Ogura, S. Itoh, J. Am. Chem. Soc. 2008, 130, 4244
94. M. Taki, S. Teramae, S. Nagatomo, Y. Tachi, T. Kitagawa, S. Itoh, S. Fukuzumi, J. Am. Chem. Soc. 2002, 124, 6367
95. N. W. Aboelella, B. F. Gherman, L. M. R. Hill, J. T. York, H. Holm, V. G. Young, Jr, C. J. Cramer, W. B. Tolman, J. Am. Chem. Soc. 2006, 128, 3445.
96. F. C. Sequeira, B. W. Turnpenny, S. R. Chemler, Angew. Chem. 2010, 122, 6509
97. Angew. Chem. Int. Ed. 2010, 49, 6365
98. W. Zeng, S. R. Chemler, J. Am. Chem. Soc. 2007, 129, 12948
99. P. H. Fuller, J.-W. Kim, S. R. Chemler, J. Am. Chem. Soc. 2008, 130, 17638.
100. P. Renaud, M. P. Sibi, Radicals in Organic Synthesis, Wiley-VCH, Weinheim, 2001
101. D. J. Rawlinson, G. Sosnovsky, Synthesis 1972, 1, and references therein.
102. Y.-X. Chen, L.-F. Qian, W. Zhang, B. Han, Angew. Chem. 2008, 120, 9470
103. Angew. Chem. Int. Ed. 2008, 47, 9330
104. G. Speier, L. Párkányi, J. Org. Chem. 1986, 51, 218.
105. L. Simándi, T. M. Simándi, Z. May, G. Besenyei, Coord. Chem. Rev. 2003, 245, 85
106. K. Schank, H. Beck, F. Werner, Helv. Chim. Acta 2000, 83, 1611.