Synthesis of β-, γ-, and δ-lactams via Pd(II)-catalyzed C-H activation reactions

Journal of the American Chemical Society

Volumn 130, Issue 43, 2008, Pages 14058-14059

  Wasa, Masayuki ^a   Yu, Jin Quan ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; CARBON; GAMMA LACTAM DERIVATIVE; HYDROGEN; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

ACETATES; CATALYSIS; COPPER; LACTAMS; MOLECULAR STRUCTURE; PALLADIUM; SILVER COMPOUNDS; STEREOISOMERISM;

EID: 54849436434     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807129e     Document Type: Article

References (21)

1. (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. For recent development of Pd(II)/Pd(IV) catalysis, see:(a) Dick, A. R.; Sanford. M. S. Tetrahedron 2006, 62, 2439.
5. (b) Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041.
6. (c) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382.
7. (a) Whitfield, S. R.; Sanford, M. S. Organometallics 2008, 27, 1683.
8. (b) Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452.
9. For the preparation of γ-benzolactams via Pd-catalyzed C-H activation/carbonylation of benzylamine derivatives, see: Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342.
10. For the intramolecular carbene insertion into C-H bonds adjacent to nitrogen atoms of diazoacetamides catalyzed by dirhodium(II) carboxylates, see: (a) Watanabe, N.; Anada, M.; Hashimoto, S.-i.; Ikegami, S. Synlett 1994, 1031.
11. (b) Doyle, M. P.; Kalinin, A. V. Synlett 1995, 1075.
12. Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190.
13. 2-catalyzed C-H bond chlorination, see: Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
14. 2 for C-H bond chlorination, see: (a) Andrienko, D. S.; Goncharov, V. S.; Raida, V. S. Russian J. Org. Chem. 1996, 32, 89.
15. (b) Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416.
16. (a) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 5961.
17. (b) Dangel, B. D.; Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2001, 123, 8149.
18. Hovelmann, C.-H.; Streuff, J.; Brelot, L.; Muniz, K. Chem. Commun. 2008, 2334.
19. Kawase, M.; Kitamura, T.; Kikugawa, Y. J. Org. Chem. 1989, 54, 3394-3403.
20. Yang, H. W.; Romo, D. J. Org. Chem. 1999, 64, 7657.
21. Bachrach, S. M. J. Org. Chem. 2008, 73, 2466.