Selective Carbon-Carbon Bond Formation via Transition Metal Catalysis. 3. A Highly Selective Synthesis of Unsymmetrical Biaryls and Diarylmethanes by the Nickel- or Palladium-Catalyzed Reaction of Aryl- and Benzylzinc Derivatives with Aryl Halides

Journal of Organic Chemistry

Volumn 42, Issue 10, 1977, Pages 1821-1823

  Negishi, Ei ichi ^a   King, Anthony O ^a   Okukado, Nobuhisa ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847088408     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00430a041     Document Type: Letter

References (24)

1. Part 1: E. Negishi and S. Baba, J. Chem. Soc., Chem. Commun., 596 (1976).
2. part 2: S. Baba and E. Negishi, J. Am. Chem. Soc., 98, 6729 (1976).
3. R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 144 (1972).
4. K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972).
5. M. F. Semmelhack, R. D. Stauffer, and T. D. Rogerson, Tetrahedron Lett., 4519 (1973).
6. M. F. Semmelhack, B. P. Chong, R. D. Stauffer, T. D. Rogerson, A. Chong, and L. D. Jones, J. Am. Chem. Soc., 97, 2507 (1975).
7. G. W. Parshall, J. Am. Chem. Soc., 96, 2360 (1974).
8. D. G. Morrell and J. K. Kochi, J. Am. Chem. Soc., 97, 7262 (1975).
9. M. Yamamura, I. Morltani, and S.-I. Murahashi, J. Organometal. Chem., 91, C39 (1975).
10. L. Cassar, J. Organometal. Chem., 93, 253 (1975).
11. H. A. Dieck and F. R. Heck, J. Organometal. Chem., 93, 259 (1975).
12. G. H. Posner, Org. React., 22, 253 (1975).
13. K. Tamao, A. Minato, N. Miyake, T. Matsuda, Chem. Lett., 133 (1975).
14. R. L. Cough, P. Mison, and J. D. Roberts, J. Org. Chem., 41, 2252 (1976).
15. A. Sekiya and N. Ishikawa, J. Organometal. Chem., 118, 349 (1976).
16. J. H. Levison and S. D. Robinson, Inorg. Synth., 13, 105 (1972).
17. “Handbook of Chemistry and Physics”, 53rd ed, R. C. Weast, Ed., The Chemical Rubber Co., Cleveland, Ohio, 1972-1973.
18. K. Ziegler and F. Dersch, Chem. Ber., 84, 448 (1931).
19. M. Gaudemar, Bull. Soc. Chim. Fr., 974 (1962).
20. S. S. Hall and F. J. McEnroe, J. Org. Chem., 40, 271 (1975).
21. G. Wittig and H. Witt, Chem. Ber., 74, 1474 (1941).
22. M. S. Kharasch and O. Reinmuth, “Grlgnard Reactions of Nonmetallic Substances”, Prentice-Hall, New York, N.Y., 1954, p 1102.
23. F. A. Drahowzal in “Friedel-Crafts and Related Reactions”, Vol. II, Part 1, G. A. Olah, Ed., Interscience, New York, N.Y., 1964, Chapter 17.
24. K. Dey, C. Eaborn, and D. R. M. Walton, Organometal. Chem. Synth., 1, 151 (1970-71).