Direct benzylic alkylation via Ni-catalyzed selective benzylic sp 3 C-O activation

Journal of the American Chemical Society

Volumn 130, Issue 11, 2008, Pages 3268-3269

  Guan, Bing Tao ^a   Xiang, Shi Kai ^a,b   Wang, Bi Qin ^a,b   Sun, Zuo Peng ^a,b   Wang, Yang ^c   Zhao, Ke Qing ^b   Shi, Zhang Jie ^a,d  

^a PEKING UNIVERSITY   (China)

^b SICHUAN NORMAL UNIVERSITY   (China)

^c CHINA AGRICULTURAL UNIVERSITY   (China)

^d INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; DISSOCIATION; ENERGY; METHYLATION;

EID: 41449112963     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710944j     Document Type: Article

References (26)

1. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
2. (b) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
3. (c) Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
4. (d) Tamao, K. J. Organomet. Chem. 2002, 653, 23.
5. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176 and references therein.
6. (b) Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049-3051.
7. (c) Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058.
8. (a) Luh, T.; Leung, M.; Wong, K. Chem. Rev. 2000, 100, 3187.
9. (b) Matthew, R. N.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525.
10. (c) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674, and references therein.
11. (a) Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
12. (b) Dankwardt, J. W. Angew. Chem., Int. Ed. 2004, 43, 2428-2432.
13. (c) Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449.
14. (d) Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894.
15. (a) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707.
16. (b) Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128, 16516-16517.
17. Guan, B.; Xiang, S.; Wu, T.; Wang, B.; Zhao, K.; Shi, Z. Chem. Commun. 2008, online.
18. (a) Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
19. (b) Matthew, R. N.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910.
20. (c) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527.
21. (d) Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.; Kambe, N. Angew. Chem., Int. Ed. 2004, 43, 6180.
22. (e) Terao, J.; Naitoh, Y.; Kuniyasu, H.; Kambe, N. Chem. Commun. 2007, 825.
23. (a) Nomura, N.; Rajianbabu, T. V. Tetrahedron Lett. 1997, 38, 1713.
24. (b) Chung, K.; Miyake, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 15.
25. (c) Kimura, M.; Futamata, M.; Mukai, R.; Tamara, Y. J. Am. Chem. Soc. 2005, 127, 4592.
26. (d) Kayaki, Y.; Koda, T.; Ikariya, T. Eur. J. Org. Chem. 2004, 24, 4989.