β-aryl eliminations from Rh(I) iminyl complexes

Journal of the American Chemical Society

Volumn 127, Issue 33, 2005, Pages 11618-11619

  Zhao, Pinjing ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; RHODIUM COMPLEX;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CONFORMATION; ELIMINATION REACTION; STEREOCHEMISTRY;

CRYSTALLOGRAPHY, X-RAY; IMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM;

EID: 23944510195     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054132+     Document Type: Article

References (30)

1. For reviews on transition metal-mediated C-C activations, see: (a) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610.
2. (b) Murakami, M.;: Ito, Y. Top. Organomet. Chem. 1999, 3, 97.
3. (c) Milstein, D.; Rybtchinski, B. Angew. Chem., Int. Ed. 1999, 38, 870.
4. Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3344.
5. (a) Kondo, T.; Kodoi, K.; Nishinaga, E., Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T.-a. J. Am. Chem. Soc. 1998, 120, 5587.
6. (b) Chow, H.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y. J. Org. Chem. 2001, 66, 1910.
7. (c) Nishimura, T.; Araki, H.; Maeda, Y.; Uemura, S. Org. Lett. 2003, 5, 2997.
8. (d) Nishimura, T.; Uemura, S. Synlett 2004, 201 and references therein.
9. (e) Nishimura, T.; Nishiguchi, Y.; Maeda, Y.; Uemura, S. J. Org. Chem. 2004, 69, 5342.
10. (f) Wakui, H.; Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2004, 126, 8658.
11. For C-C cleavage of an amine by a pathway other than β-elimination, see: Zhang, X.; Emge, T. J.; Ghosh, R.; Goldman, A. S.; J. Am. Chem. Soc 2005, 127, 8250.
12. (a) Erker, G.; Fromberg, W.; Kruger, C.; Raabe, E. J. Am. Chem. Soc. 1988, 110, 2400 and references therein.
13. (b) Esteruelas, M. A.; Lahoz, F. J.; Olivan, M.; Onate, E.; Oro, L. A. Organometallics 1994, 13, 3315.
14. (c) Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2694.
15. (d) Ferreira, C. M. P.; Guedes da Silva, M. P.; Kukushkin, V. Y.; Frausto da Silva, J. J. R.; Pombeiro, A. J. L. J. Chem. Soc., Dalton Trans. 1998, 325.
16. Traces of the corresponding biaryls and arenes were also observed. Heating of isolated 3a-d formed the same byproducts.
17. 3-ligated square-planar Rh(I) alkyl complex, see: Price, R. T.; Andersen, R. A.;: Muetterties, F. L. J. Organomet. Chem. 1989, 376, 407.
18. For a discussion of α-substitution effects in Pd-catalyzed β-aryl elimination via proposed alkoxide intermediates, see: Terao, Y.; Wakui, H.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 5236 and references therein.
19. 3RhCl with the corresponding aryllithium or Grignard reagents in 55-77% isolated yields (see Supporting Information).
20. During the review of this manuscript, we obtained X-ray structural data on complex 3e that shows the absence of a Rh-O bonding interaction. Details will be reported in future publications.
21. For catalytic processes that are proposed to occur by the insertion of a nitrile into a late metal aryl or alkenyl linkage see: (a) Zhou, C. X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302.
22. (b) Miura, T.; Nakazawa, H.; Murakami, M. Chem. Commun. 2005, 2855.
23. (c) Miura, T.; Murakami, M. Org. Lett. 2005, 7, 3339.
24. (a) Whitesides, G. M.; Gaasch, J. F.; Stedronsky, E. R. J. Am. Chem. Soc. 1972, 94, 5258.
25. (b) Evans, J.; Schwartz, J. Urquhart, P. W. J. Organomet. Chem. 1974, 81, C37.
26. (c) Ozawa, F.; Ito, T.; Yamamoto, Y. J. Am. Chem. Soc. 1980, 102, 6457.
27. (d) Cross, R. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; John Wiley: New York. 1985; Vol. 2, p 559.
28. (e) Miller, T. M.; Whitesides, G. M. Organometallics 1986, 5, 1473.
29. (a) Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7010.
30. (b) Zhao, J.; Hesslink, H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 7220.