Promotion of reductive elimination reaction of diorgano(2,2′-bipyridyl)nickel(II) complexes by electron-accepting aromatic compounds, Lewis acids, and Brønsted acids

Bulletin of the Chemical Society of Japan

Volumn 75, Issue 9, 2002, Pages 1997-2009

  Yamamoto, Takakazu ^a   Abla, Mahmut ^a   Murakami, Yasuharu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; COORDINATION REACTIONS; MOLECULAR WEIGHT; ULTRAVIOLET SPECTROSCOPY;

ELIMINATION REACTION;

NICKEL;

ALKYL GROUP; AROMATIC COMPOUND; DIORGANO(2,2' BIPYRIDYL)NICKEL; LEWIS ACID; NICKEL COMPLEX; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON; EQUILIBRIUM CONSTANT; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; ULTRAVIOLET SPECTROSCOPY;

EID: 0036388663     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.75.1997     Document Type: Article

References (87)

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6. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
7. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
8. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
9. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
10. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
11. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
12. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
13. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
14. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
15. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
16. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
17. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
18. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
19. For diorganonickel(II) complexes, e.g., a) T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 and 3360 (1971). b) T. Yamamoto, Y. Nakamura, and A. Yamamoto, Bull. Chem. Soc. Jpn., 49, 191 (1976). c) M. Uchino, K. Asagi, A. Yamamoto, and S. Ikeda, J. Organomet. Chem., 84, 93 (1975); d) B. Åkermark, H. Johansen, B. Roos, and U. Wahlgren, J. Am. Chem. Soc., 101, 5876 (1979). e) P. Binger and M. Doyle, J. Organomet. Chem., 162, 195 (1978). f) M. J. Doyle, J. McMeeking, and P. Binger, J. Chem. Soc., Chem. Commun., 1976, 376. g) H. Hoberg and A. Herrera, A. Angew. Chem., Int. Ed. Engl., 19, 927 (1980). h) S. Komiya, Y. Abe, A. Yamamoto, and T. Yamamoto, Organometallics, 2, 1466 (1983). i) T. Kohara, T. Yamamoto, and A. Yamamoto, J. Organometal. Chem., 192, 265 (1980). j) B. Åkermark and A. Ljungqvist, J. Organomet. Chem., 149, 97 (1978). k) T. Yamamoto, J. Ishizu, T. Kohara, S. Komiya, and A. Yamamoto, J. Am. Chem. Soc., 102, 3758 (1980). l) K. Tatsumi, A. Nakamura, S. Komiya, A. Yamamoto, and T. Yamamoto, J. Am. Chem. Soc., 106, 8181 (1984). m) T. Yamamoto and A. Yamamoto, J. Organomet. Chem., 57, 127 (1973). n) S. Komiya, Y. Arai, K. Tanaka, T. Yamamoto, and A. Yamamoto, Organometallics, 4, 1130 (1985).
20. For diorganopalladium(II) complexes, e.g., a) J. F. Hartwig, S. Richards, D. Barañano, and F. Paul, J. Am. Chem. Soc., 118, 3626 (1996). b) R. A. Widenhoefer, H. A. Zhong, and S. L. Buchwald, J. Am. Chem. Soc., 119, 6787 (1997). c) F. Ozawa, K. Kurihara, T. Yamamoto, and A. Yamamoto, Bull. Chem. Soc. Jpn., 58, 399 (1985). d) K. Osakada, R. Sakata, and T. Yamamoto, Organometallics, 16, 5354 (1997). e) F. Ozawa, K. Hidaka, T. Yamamoto, and A. Yamamoto, J. Organomet. Chem., 330, 253 (1987). f) T. Yamamoto, O. Saito, and A. Yamamoto, J. Am. Chem. Soc., 103, 5600 (1981).
21. For diorganopalladium(II) complexes, e.g., a) J. F. Hartwig, S. Richards, D. Barañano, and F. Paul, J. Am. Chem. Soc., 118, 3626 (1996). b) R. A. Widenhoefer, H. A. Zhong, and S. L. Buchwald, J. Am. Chem. Soc., 119, 6787 (1997). c) F. Ozawa, K. Kurihara, T. Yamamoto, and A. Yamamoto, Bull. Chem. Soc. Jpn., 58, 399 (1985). d) K. Osakada, R. Sakata, and T. Yamamoto, Organometallics, 16, 5354 (1997). e) F. Ozawa, K. Hidaka, T. Yamamoto, and A. Yamamoto, J. Organomet. Chem., 330, 253 (1987). f) T. Yamamoto, O. Saito, and A. Yamamoto, J. Am. Chem. Soc., 103, 5600 (1981).
22. For diorganopalladium(II) complexes, e.g., a) J. F. Hartwig, S. Richards, D. Barañano, and F. Paul, J. Am. Chem. Soc., 118, 3626 (1996). b) R. A. Widenhoefer, H. A. Zhong, and S. L. Buchwald, J. Am. Chem. Soc., 119, 6787 (1997). c) F. Ozawa, K. Kurihara, T. Yamamoto, and A. Yamamoto, Bull. Chem. Soc. Jpn., 58, 399 (1985). d) K. Osakada, R. Sakata, and T. Yamamoto, Organometallics, 16, 5354 (1997). e) F. Ozawa, K. Hidaka, T. Yamamoto, and A. Yamamoto, J. Organomet. Chem., 330, 253 (1987). f) T. Yamamoto, O. Saito, and A. Yamamoto, J. Am. Chem. Soc., 103, 5600 (1981).
23. For diorganopalladium(II) complexes, e.g., a) J. F. Hartwig, S. Richards, D. Barañano, and F. Paul, J. Am. Chem. Soc., 118, 3626 (1996). b) R. A. Widenhoefer, H. A. Zhong, and S. L. Buchwald, J. Am. Chem. Soc., 119, 6787 (1997). c) F. Ozawa, K. Kurihara, T. Yamamoto, and A. Yamamoto, Bull. Chem. Soc. Jpn., 58, 399 (1985). d) K. Osakada, R. Sakata, and T. Yamamoto, Organometallics, 16, 5354 (1997). e) F. Ozawa, K. Hidaka, T. Yamamoto, and A. Yamamoto, J. Organomet. Chem., 330, 253 (1987). f) T. Yamamoto, O. Saito, and A. Yamamoto, J. Am. Chem. Soc., 103, 5600 (1981).
24. For diorganopalladium(II) complexes, e.g., a) J. F. Hartwig, S. Richards, D. Barañano, and F. Paul, J. Am. Chem. Soc., 118, 3626 (1996). b) R. A. Widenhoefer, H. A. Zhong, and S. L. Buchwald, J. Am. Chem. Soc., 119, 6787 (1997). c) F. Ozawa, K. Kurihara, T. Yamamoto, and A. Yamamoto, Bull. Chem. Soc. Jpn., 58, 399 (1985). d) K. Osakada, R. Sakata, and T. Yamamoto, Organometallics, 16, 5354 (1997). e) F. Ozawa, K. Hidaka, T. Yamamoto, and A. Yamamoto, J. Organomet. Chem., 330, 253 (1987). f) T. Yamamoto, O. Saito, and A. Yamamoto, J. Am. Chem. Soc., 103, 5600 (1981).
25. For diorganopalladium(II) complexes, e.g., a) J. F. Hartwig, S. Richards, D. Barañano, and F. Paul, J. Am. Chem. Soc., 118, 3626 (1996). b) R. A. Widenhoefer, H. A. Zhong, and S. L. Buchwald, J. Am. Chem. Soc., 119, 6787 (1997). c) F. Ozawa, K. Kurihara, T. Yamamoto, and A. Yamamoto, Bull. Chem. Soc. Jpn., 58, 399 (1985). d) K. Osakada, R. Sakata, and T. Yamamoto, Organometallics, 16, 5354 (1997). e) F. Ozawa, K. Hidaka, T. Yamamoto, and A. Yamamoto, J. Organomet. Chem., 330, 253 (1987). f) T. Yamamoto, O. Saito, and A. Yamamoto, J. Am. Chem. Soc., 103, 5600 (1981).
26. For organoplatinum(II) complexes, e.g., a) P. S. Braterman, and R. J. Cross, G. B. Young, J. Chem. Soc. Dalton Trans., 1976, 1306 and 1310. b) D. M. Crumpton, K. I. Goldberg, J. Am. Chem. Soc., 122, 962 (2000).
27. For organoplatinum(II) complexes, e.g., a) P. S. Braterman, and R. J. Cross, G. B. Young, J. Chem. Soc. Dalton Trans., 1976, 1306 and 1310. b) D. M. Crumpton, K. I. Goldberg, J. Am. Chem. Soc., 122, 962 (2000).
28. Ni promoted; e.g., a) K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972). b) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada, Bull. Chem. Soc. Jpn., 49, 1958 (1976). c) R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144. d) M. F. Semmelhack, P. M. Helquest, and L. D. Jones, J. Am. Chem. Soc., 93, 5903 (1971). e) T. Yamamoto, S. Wakabayashi, and K. Osakada, J. Organomet. Chem., 428, 223 (1992). f) J. Terao, H. Watanabe, A. Ikuma, H. Kuniyasu, and N. Kanbe, J. Am. Chem. Soc., 124, 4222 (2002) (published after submission (during revision) of this paper).
29. Ni promoted; e.g., a) K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972). b) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada, Bull. Chem. Soc. Jpn., 49, 1958 (1976). c) R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144. d) M. F. Semmelhack, P. M. Helquest, and L. D. Jones, J. Am. Chem. Soc., 93, 5903 (1971). e) T. Yamamoto, S. Wakabayashi, and K. Osakada, J. Organomet. Chem., 428, 223 (1992). f) J. Terao, H. Watanabe, A. Ikuma, H. Kuniyasu, and N. Kanbe, J. Am. Chem. Soc., 124, 4222 (2002) (published after submission (during revision) of this paper).
30. Ni promoted; e.g., a) K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972). b) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada, Bull. Chem. Soc. Jpn., 49, 1958 (1976). c) R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144. d) M. F. Semmelhack, P. M. Helquest, and L. D. Jones, J. Am. Chem. Soc., 93, 5903 (1971). e) T. Yamamoto, S. Wakabayashi, and K. Osakada, J. Organomet. Chem., 428, 223 (1992). f) J. Terao, H. Watanabe, A. Ikuma, H. Kuniyasu, and N. Kanbe, J. Am. Chem. Soc., 124, 4222 (2002) (published after submission (during revision) of this paper).
31. Ni promoted; e.g., a) K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972). b) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada, Bull. Chem. Soc. Jpn., 49, 1958 (1976). c) R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144. d) M. F. Semmelhack, P. M. Helquest, and L. D. Jones, J. Am. Chem. Soc., 93, 5903 (1971). e) T. Yamamoto, S. Wakabayashi, and K. Osakada, J. Organomet. Chem., 428, 223 (1992). f) J. Terao, H. Watanabe, A. Ikuma, H. Kuniyasu, and N. Kanbe, J. Am. Chem. Soc., 124, 4222 (2002) (published after submission (during revision) of this paper).
32. Ni promoted; e.g., a) K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972). b) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada, Bull. Chem. Soc. Jpn., 49, 1958 (1976). c) R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144. d) M. F. Semmelhack, P. M. Helquest, and L. D. Jones, J. Am. Chem. Soc., 93, 5903 (1971). e) T. Yamamoto, S. Wakabayashi, and K. Osakada, J. Organomet. Chem., 428, 223 (1992). f) J. Terao, H. Watanabe, A. Ikuma, H. Kuniyasu, and N. Kanbe, J. Am. Chem. Soc., 124, 4222 (2002) (published after submission (during revision) of this paper).
33. Ni promoted; e.g., a) K. Tamao, K. Sumitani, and M. Kumada, J. Am. Chem. Soc., 94, 4374 (1972). b) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada, Bull. Chem. Soc. Jpn., 49, 1958 (1976). c) R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144. d) M. F. Semmelhack, P. M. Helquest, and L. D. Jones, J. Am. Chem. Soc., 93, 5903 (1971). e) T. Yamamoto, S. Wakabayashi, and K. Osakada, J. Organomet. Chem., 428, 223 (1992). f) J. Terao, H. Watanabe, A. Ikuma, H. Kuniyasu, and N. Kanbe, J. Am. Chem. Soc., 124, 4222 (2002) (published after submission (during revision) of this paper).
34. Pd promoted; e.g., a) A. Sekiya and N. Ishikawa, J. Organomet. Chem., 118, 349 (1976); b) J. K. Stille, Angew. Chem., 98, 504 (1986). c) H. A. Dieck and R. F. Heck, J. Organomet. Chem., 93, 259 (1975). d) K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett., 16, 4467 (1975). e) N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
35. Pd promoted; e.g., a) A. Sekiya and N. Ishikawa, J. Organomet. Chem., 118, 349 (1976); b) J. K. Stille, Angew. Chem., 98, 504 (1986). c) H. A. Dieck and R. F. Heck, J. Organomet. Chem., 93, 259 (1975). d) K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett., 16, 4467 (1975). e) N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
36. Pd promoted; e.g., a) A. Sekiya and N. Ishikawa, J. Organomet. Chem., 118, 349 (1976); b) J. K. Stille, Angew. Chem., 98, 504 (1986). c) H. A. Dieck and R. F. Heck, J. Organomet. Chem., 93, 259 (1975). d) K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett., 16, 4467 (1975). e) N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
37. Pd promoted; e.g., a) A. Sekiya and N. Ishikawa, J. Organomet. Chem., 118, 349 (1976); b) J. K. Stille, Angew. Chem., 98, 504 (1986). c) H. A. Dieck and R. F. Heck, J. Organomet. Chem., 93, 259 (1975). d) K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett., 16, 4467 (1975). e) N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
38. Pd promoted; e.g., a) A. Sekiya and N. Ishikawa, J. Organomet. Chem., 118, 349 (1976); b) J. K. Stille, Angew. Chem., 98, 504 (1986). c) H. A. Dieck and R. F. Heck, J. Organomet. Chem., 93, 259 (1975). d) K. Sonogashira, Y. Tohda, and N. Hagihara, Tetrahedron Lett., 16, 4467 (1975). e) N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
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