Highly efficient copper-catalyzed nitro-Mannich type reaction: Cross-dehydrogenative-coupling between sp3 C-H bond and sp 3 C-H bond

Journal of the American Chemical Society

Volumn 127, Issue 11, 2005, Pages 3672-3673

  Li, Zhiping ^a   Li, Chao Jun ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; COPPER;

ARTICLE; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; DEHYDROGENATION; MANNICH REACTION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION OPTIMIZATION;

EID: 15744372304     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050058j     Document Type: Article

References (37)

1. For representative reviews, see: (a) Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083.
2. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
3. (c) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
4. (d) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
5. (e) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
6. (f) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson T. H. Acc. Chem. Res. 1995, 28, 154.
7. Diederich, F., Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998.
8. 3 C-H and sp C-H: (a) Li, Z.; Li, C.-J. Org. Lett. 2004, 6, 4997.
9. (b) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810.
10. (c) Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312.
11. (d) Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. J. Chem. Res., Miniprint 1993, 2827.
12. 2 C-H: (a) Hatamoto, Y.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2004, 6, 4623.
13. (b) Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476.
14. (c) Reference 1c.
15. (d) Tsuji, J.; Nagashima, H. Tetrahedron 1984, 40, 2699.
16. 3 C-H: (a) DeBoef, B.; Pastine, S. J.; Sames, D. J. Am. Chem. Soc. 2004, 126, 6556.
17. (b) Lin, Y.; Ma, D.; Lu, X., Tetrahedron Lett. 1987, 28, 3249.
18. (D) sp C-H and sp C-H: (a) Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E. J. Am. Chem. Soc. 1982, 104, 5560.
19. (b) Nicolaou, K. C.; Zipkin, R. E.; Petasis, N. A. J. Am. Chem. Soc. 1982, 104, 5558.
20. (c) Nicolaou, K. C.; Petasis, N. A.; Uenishi, J.; Zipkin, R. E.; J. Am. Chem. Soc. 1982, 104, 5557.
21. (d) Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E.; Uenishi, J. J. Am. Chem. Soc. 1982, 104, 5555.
22. 3 C-H has been reported. In this case, however, two homo-cross-coupling products could not be avoided, see: Brown, S. H.; Crabtree, R. H. J. Am. Chem. Soc. 1989, 111, 2935.
23. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
24. Baer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Group; Patai, S., Ed.; Interscience: New York, 1970; Part 2, 1117.
25. (a) Bernardi, L.; Bonini, B. F.; Capito, E.; Dessole, G.; Comes-Franchini, M.; Fochi, M.; Ricci, A. J. Org. Chem. 2004, 69, 8168 and references therein,
26. (b) Adams, H.; Anderson, J. C.; Peace, S.; Pennell, A. M. K. J. Org. Chem. 1998, 63, 9932.
27. Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017 and references therein.
28. Yao, X.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 6884.
29. Relatively low isolated yields are due to the decomposition of the products when the reaction mixtures were separated by column chromatography.
30. Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. J. Chem. Res. (M) 1993, 2827. Other oxidants, such as elemental iodine, are known to oxidize tetrahydroisoquinolines to quinolinium intermediates, see: Leonard, N. J.; Leubner, G. W. J. Am. Chem. Soc. 1949, 71, 3408.
31. Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. J. Chem. Res. (M) 1993, 2827. Other oxidants, such as elemental iodine, are known to oxidize tetrahydroisoquinolines to quinolinium intermediates, see: Leonard, N. J.; Leubner, G. W. J. Am. Chem. Soc. 1949, 71, 3408.
32. (a) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692.
33. (b) Christensen, C.; Juhl, K.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4875 and references therein.
34. For a recent review, see: (c) Luzio, F. A. Tetrahedron 2001, 57, 915.
35. (d) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
36. (a) Murahashi, S.-I.; Naota, T.; Kuwabara, T.; Saito, T.; Kumobayashi, H.; Akutagawa. S. J. Am. Chem. Soc. 1990, 112, 7820.
37. (b) Murahashi, S.-I.; Naota, T.; Yonemura, K. J. Am. Chem. Soc. 1988, 110, 8256.