Pd(II)-catalyzed amination of C-H bonds using single-electron or two-electron oxidants

Journal of the American Chemical Society

Volumn 131, Issue 31, 2009, Pages 10806-10807

  Mei, Tian Sheng ^a   Wang, Xisheng ^a   Yu, Jin Quan ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

C-H BOND; CATALYTIC REACTIONS; CHEMICAL EQUATIONS; INTRAMOLECULAR AMINATION; NITRO GROUP; REACTION PROTOCOLS; SINGLE ELECTRON; TWO-ELECTRON OXIDANTS;

AMINATION; AMINES; CATALYSIS; OXIDANTS; PALLADIUM;

PALLADIUM COMPOUNDS;

INDOLE DERIVATIVE; OXIDIZING AGENT; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON; SUBSTITUTION REACTION; SYNTHESIS;

AMINATION; CATALYSIS; ELECTRONS; INDOLES; OXIDANTS; PALLADIUM;

EID: 68249138163     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904709b     Document Type: Article

References (31)

1. For Pd-catalyzed amination of C-H bonds see: (a) Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560.
2. (b) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
3. (c) Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931.
4. (d) Yamamoto, M.; Matsubara, S. Chem. Lett. 2007, 36, 172.
5. (e) Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
6. (f) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
7. (g) Liu, G. S.; Yin, G. Y.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733.
8. (h) Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115.
9. For examples of Cu(II)-catalyzed C-H amination reactions: (a) Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
10. (b) Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842.
11. (c) Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932.
12. For a highly efficient C-H borylation and amination sequence, see: Tzschucke, C. C.; Murphy, J. M.; Hartwig, J. F. Org. Lett. 2007, 9, 761.
13. For metal-catalyzed nitrene insertions into C-H bonds, see: (a) Espino, C. G.; Du Bois, J. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VHC: Weinheim, Germany, 2005; pp 379-416.
14. (b) He, L.; Chan, P. W. H.; Tsui, W.-M.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2004, 6, 2405.
15. (c) Liang, C. G.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
16. For recent reviews on C-H functionalizations via various Pd catalysis, see: (a) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
17. (b) Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041.
18. (c) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382.
19. For two rare examples of such amination involving specific amides and anilines, see: (a) Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058.
20. (b) Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184.
21. Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452.
22. For insightful investigations into competitive reductive elimination of amino and chloro groups from Pd(IV) centers, see: (a) Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142.
23. (b) Whitfield, S. R.; Sanford, M. S. Organometallics 2008, 27, 1683.
24. (a) Cotton, F. A.; Koshevoy, I. O.; Lahuerta, P.; Murillo, C. A.; Sanaú, M.; Ubeda, M. A.; Zhao, Q. L. J. Am. Chem. Soc. 2006, 128, 13674.
25. (b) McAuley, A.; Whitcombe, T. W. Inorg. Chem. 1988, 27, 3090.
26. (a) Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134.
27. (b) Kaspi, A. W.; Yahav-Levi, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2008, 47, 5.
28. (c) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060.
29. (a) Harrington, P. J.; Hegedus, L. S. J. Org. Chem. 1984, 49, 2657.
30. (b) Liras, S.; Lynch, C. L.; Fryer, A. M.; Vu, B. T.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 5918.
31. (c) Kalinin, A. V.; Chauder, B. A.; Rakhit, S.; Snieckus, V. Org. Lett. 2003, 5, 3519.