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Volumn 109, Issue 8, 1987, Pages 2393-2401

Palladium- or Nickel-Catalyzed Reactions of Alkenylmetals with Unsaturated Organic Halides as a Selective Route to Arylated Alkenes and Conjugated Dienes: Scope, Limitations, and Mechanism1,2

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Indexed keywords


EID: 33845282857     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00242a024     Document Type: Article
Times cited : (297)

References (31)
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    • Reported in preliminary communications. (b) Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729. (c) Negishi, E.; Van Horn, D. E. J. Am. Chem. Soc. 1977, 99, 3168. (d) Okukado, N.; Van Horn, D. E.; Klima, W. E.; Negishi, E. Tetrahedron Lett. 1978 1027.
    • Reported in preliminary communications. (a) Negishi, E.; Baba, S. J. Chem. Soc., Chem. Commun. 1976, 596. (b) Baba, S.; Negishi, E. J. Am. Chem. Soc. 1976, 98, 6729. (c) Negishi, E.; Van Horn, D. E. J. Am. Chem. Soc. 1977, 99, 3168. (d) Okukado, N.; Van Horn, D. E.; Klima, W. E.; Negishi, E. Tetrahedron Lett. 1978 1027.
    • (1976) J. Chem. Soc., Chem. Commun. , pp. 596
    • Negishi, E.1    Baba, S.2
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    • For a review, see
    • For a review, see: Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
    • (1981) Pure Appl. Chem. , vol.53 , pp. 2333
    • Negishi, E.1
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    • The following organoboron methodologies were known, each probably representing the first highly selective method of some generality: E,E-dienes, Negishi, E.; Yoshida, T. J. Chem. Soc., Chem. Commun. 1973, 636; E,Z-dienes, Negishi, E.; Lew, G.; Yoshida, T. J. Chem. Soc., Chem. Commun. 1973, 874; Z,Z-dienes, Zweifel, G.; Polston, N. L. J. Am. Chem. Soc. 1070, 92, 4068. (b) A very limited number of examples of copper-promoted alkenyl-alkenyl cross coupling were known. They were either low-yielding or nonselective: Posner, G. H. Org. React. 1975, 22, 253.
    • J. Chem. Soc., Chem. Commun. , vol.92 , pp. 4068
    • Negishi, E.1    Yoshida, T.2
  • 14
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    • (b) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551 and references therein.
    • Kosugi, M.; Sasazawa, K.; Shimizu, I.; Migita, T. Chem. Lett. 1977, 301. (b) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992. (c) Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551 and references therein.
    • (1977) Chem. Lett. , pp. 301
    • Kosugi, M.1    Sasazawa, K.2    Shimizu, I.3    Migita, T.4
  • 15
    • 0000725865 scopus 로고
    • For the palladium-catalyzed reaction of alkenyltins with alkenyl triflates, see
    • For the palladium-catalyzed reaction of alkenyltins with alkenyl triflates, see: Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4630
    • Scott, W.J.1    Crisp, G.T.2    Stille, J.K.3
  • 16
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    • (b) Normant, J. F.; Alexakis, A. In Current Trends in Organic Synthesis: Nozaki, H., Ed., Pergamon : Oxford, 1982; p 291.
    • Jabri, N.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1981, 22, 959. (b) Normant, J. F.; Alexakis, A. In Current Trends in Organic Synthesis: Nozaki, H., Ed., Pergamon: Oxford, 1982; p 291.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 959
    • Jabri, N.1    Alexakis, A.2    Normant, J.F.3
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    • See, also: Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262.
    • Smith, G.; Kochi, J. K. J. Organomet. Chem. 1980, 198, 199. See, also: Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262.
    • (1980) J. Organomet. Chem. , vol.198 , pp. 199
    • Smith, G.1    Kochi, J.K.2
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    • (b) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (c) Moravskiy, A.; Stille, J. K. 1981, 103, 4182.
    • Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981. (b) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933. (c) Moravskiy, A.; Stille, J. K. 1981, 103, 4182.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 4981
    • Milstein, D.1    Stille, J.K.2
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    • (b) Jenkins, J. M.; Verkade, J. G. Inorg. Synth. 1968. 11, 108.
    • Booth, G. Adv. Inorg. Chem. Radiochem. 1964, 6, 1. (b) Jenkins, J. M.; Verkade, J. G. Inorg. Synth. 1968. 11, 108.
    • (1964) Adv. Inorg. Chem. Radiochem. , vol.6 , pp. 1
    • Booth, G.1


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