Highly efficient copper-catalyzed amidation of aldehydes by C-H activation

Chemistry - A European Journal

Volumn 14, Issue 34, 2008, Pages 10722-10726

  Wang, Long ^a   Fu, Hua ^a   Jiang, Yuyang ^a,b   Zhao, Yufen ^a  

^a Tsinghua University   (China)

^b TSINGHUA UNIVERSITY   (China)

Author keywords

Aldehydes; Amide bond formation; C H activation; Copper; Homogeneous catalysis

Indexed keywords

ACTIVATION ANALYSIS; ALDEHYDES; AMIDES; AMINES; ORGANIC COMPOUNDS; REACTION KINETICS;

AMIDATION; AMIDE BOND FORMATION; C-H ACTIVATION; C-H ACTIVATIONS; HIGHLY EFFICIENT; HOMOGENEOUS CATALYSIS; SYNTHESIS OF;

COPPER;

ALDEHYDE; AMIDE; COPPER; IMIDE; N BROMOSUCCINIMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; AMIDES; BROMOSUCCINIMIDE; CATALYSIS; COPPER; IMIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 56749085836     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801620     Document Type: Article

References (72)

1. a) J. Fraxedas, Molecular Organic Materials: From Molecules to Crystalline Solids, Cambridge University Press, Cambridge, 2006;
2. b) A. Kleeman, J. Engel, Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed., Thieme, Stuttgart, 2001;
3. c) J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243-2266.
4. a) C. A. G. N. Montalbetti, V. Falque, Tetrahedron 2005, 61, 10827-10852;
5. b) R. C. Larock, Comprehensive Organic Transformations, Wiley-VCH, Weinheim, 1999;
6. c) P. D. Bailey, I. D. Collier, K. M. Morgan in Comprehensive Organic Functional Group Transformations, Vol. 5 (Eds.: A. R. Katritzky, O. Meth-Cohn, C. W. Rees), Pergamon, Cambridge, 1995, Chapter 6.
7. I. E. Marko, A. Mekhalfia, Tetrahedron Lett. 1990, 31, 7237-7240.
8. K. Ishihara, T. Yano. Org. Lett. 2004, 6, 1983-1986.
9. a) L. Zhang, S. Wang, S. Zhou, G. Yang, E. Sheng, J. Org. Chem. 2006, 71, 3149-3153;
10. b) S. Y. Seo; T. J. Marks, Org. Lett. 2008, 10, 317-319;
11. T. J. Marks, Org. Lett. 2008, 10, 317-319.
12. a) H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796-13797;
13. b) J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798-13799.
14. a) W. Yoo, C. Li, J. Am. Chem. Soc. 2006, 128, 13064-13065;
15. b) A. Tillack, I. Rudloff, M. Beller, Eur. J. Org. Chem. 2001, 523-528;
16. c) T. Naota, S. Murahashi, Synlett 1991, 693-694;
17. d) Y. Tamaru, Y. Yamada, Z. Yoshida, Synthesis 1983, 474-476.
18. a) K. Ekoue-Kovi, C. Wolf, Org. Lett. 2007, 9, 3429-3432;
19. b) J. Gao; G.-W. Wang, J. Org. Chem. 2008, 73, 2955-2958;
20. G.-W. Wang, J. Org. Chem. 2008, 73, 2955-2958.
21. C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790-792.
22. a) K. Godula, D. Sames, Science 2006, 312, 67-72;
23. b) R. G. Bergman, Nature 2007, 446, 391-393;
24. c) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Jr., Maleczka, M. R. Smith, III Science 2002, 295, 305-307;
25. d) H. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995-1997;
26. e) J.A. Labinger, J. E. Bercaw, Nature 2002, 417, 507-514;
27. f) Z. Li, D. S. Bohle, C-J. Li, Proc. Natl. Acad. Sci. USA 2006, 103, 8928-8933;
28. g) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810-11811;
29. h) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672-3673.
30. Representative intramolecular melal-nitrene-lype amidalions: a) M. Kim, J. V. Mulcahy, C. G. Espino, J. Du Bois, Org. Lett. 2006, 8, 1073-1076;
31. b) Y. Cui, C. He, Angew. Chem. 2004, 116, 4306-4308;
32. Angew. Chem. Int. Ed. 2004, 43, 4210-4212;
33. c) C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 2004, 126, 15378-15379;
34. d) J.-L. Liang, S.-X. Yuan, J.-S. Huang, W-Y. Yu, C.-M. Che, Angew. Chem. 2002, 114, 3615-3618;
35. Angew. Chem. Int. Ed. 2002, 41, 3465-3468;
36. e) C. G. Espino, P. M. Wehn, J. Chow, J. Du Bois, J. Am. Chem. Soc. 2001, 123, 6935-6936;
37. g) C. G. Espino, J. Du Bois, Angew. Chem. 2001, 113, 618-620;
38. Angew. Chem. Int. Ed. 2001, 40, 598-600.
39. For a review on intermolecular C-H amidations, see: a) H. M. L. Davies, Angew. Chem. 2006, 118, 6574-6577;
40. Angew. Chem. Int. Ed. 2006, 45, 6422-6425; representative intermolecular melal-nitrene-lype amidalions:
41. b) M. R. Fructos, S. Trofimenko, M. M. Díaz-Requejo, P. J. Pérez, J. Am. Chem. Soc. 2006, 128, 11784-11791;
42. c) H.-Y. Thu, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2006, 128, 9048-9049;
43. d) S. K.-Y. Leung, W.-M. Tsui, J.-S. Huang, C.-M. Che, J.-L. Liang, N. Zhu, J. Am. Chem. Soc. 2005, 127, 16629-16640.
44. For other strategies for the amidalion of allylic and benzylic C-H bonds, see: a) W. Adam, O. Krebs, Chem. Rev. 2003, 103, 4131-4146;
45. b) M. Johannsen, K. A. Jørgensen, Chem. Rev. 1998, 98, 1689-1708.
46. a) M. R. Fructos, T S. rofimenko, M. M. Díaz-Requejo, P. J. Pérez,. J. Am. Chem. Soc. 2006, 128, 11784-11791;
47. b) R. Bhuyan, K. M. Nicholas, Org. Lett. 2007, 9, 3957-3959;
48. c) D. P. Albone, S. Challenger, A. M. Derrick, S. M. Fillery, J. L. Irwin, C. M. Parsons, H. Takada, P. C. Taylor, D. J. Wilson, Org. Biomol. Chem. 2005, 3, 107-111;
49. d) G. Pelletier, D. A. Powell, Org. Lett. 2006, 8, 6031-6034;
50. e) Y. Zhang, H. Fu, Y. Jiang, Y. Zhao, Org. Lett. 2007, 9, 3813-3816.
51. a) J. W. W. Chang, P. W. H. Chan, Angew. Chem. 2008, 120, 1154-1156;
52. Angew. Chem. Int. Ed. 2008, 47, 1138-1140;
53. b) J. Chan, K. D. Baucom, J. A. Murry, J. Am. Chem. Soc. 2007, 129, 14106-14107.
54. a) K. C. Nicolaou, C. J. N. Mathison, Angew. Chem. 2005, 117, 6146-6151;
55. Angew. Chem. Int. Ed. 2005, 44, 5992-5997;
56. b) E. P. Balskus, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 6810-6812;
57. c) C. D. Vanderwal, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 14724-14725;
58. d) M. P. Sibi, G. Petrovic, J. Zimmerman, J. Am. Chem. Soc. 2005, 127, 2390-2391;
59. e) T. Inokuma, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2006, 128, 9413-9419;
60. f) M. P. Sibi, N. Prabagaran, S. G. Ghorpade, C. P. Jasperse, J. Am. Chem. Soc. 2003, 125, 11796-11797.
61. a) H. B. Maruyama, Y. Suhara, J. Suzuki-Watanabe, Y. Maeshima, N. Shimizu, M. Ogura-Hamada, H. Fujimoto, K. Takano, J. Antibiot. 1975, 28, 636-647;
62. b) Y. Suhara, H. B. Maruyama, Y. Kotoh, Y. Miyasaka, K. Yokose, H. Shirai, K. Takano, P. Quitt, P. Lanz, J. Antibiot. 1975, 28, 648-655.
63. K. Krohn, C. Franke, P. G. Jones, H.-J. Aust, S. Draeger, B. Shultz, Liebigs Ann. Chem. 1992, 789-798.
64. J. Thirkettle, E. Alvarez, H. Boyd, M. Brown, E. Diez, J. Hueso, S. Elson, M. Fulston, C. Gershater, M. L. Morata, P. Perez, S. Ready, J. M. Sanchez-Pulles, R. Sheridan, A. Stefanska, S. Warr, J. Antibiot. 2000, 53, 664-669.
65. a) Z. Wang, Y. Zhang, H. Fu, Y. Jiang, Y. Zhao, Org. Lett. 2008, 10, 1863-1866;
66. b) X. Liu, Y. Zhang, L. Wang, H. Fu, Y. Jiang, Y. Zhao, J. Org. Chem. 2008, 73, 6207-6212;
67. c) M. Niu, Z. Yin, H. Fu, Y. Jiang, Y. Zhao, J. Org. Chem. 2008, 73, 3961-3963.
68. L. Xu, S. Zhang, M. L. Trudell, Chem. Commun. 2004, 1668-1669.
69. V. Nair, S. C. Mathew, A. T. Biju, E. Suresh, Tetrahedron Lett. 2007, 48, 9018-9020.
70. T. Sueda, D. Kajishima, S. Goto, J. Org. Chem. 2003, 68, 3307-3310.
71. D. I. MaGee, M. Ramaseshan, J. D. Leach, Canadian J. Chem. 1995, 73, 2111-2118.
72. S. Dandapani, J. J. Newsome, D. P. Curran, Tetrahedron Lett. 2004, 45, 6653-6656.