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Volumn 77, Issue 5, 2004, Pages 1013-1019

The cyanation of aromatic halides catalyzed by nickel(0) complexes generated in situ. III. Kinetic and mechanistic aspects

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; NICKEL; REACTION KINETICS; ZINC COMPOUNDS;

EID: 2642536930     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.1013     Document Type: Article
Times cited : (20)

References (27)
  • 2
  • 3
    • 0000906771 scopus 로고
    • For reviews, G. P. Ellis and T. M. Ronney-Alexander, Chem. Rev., 87, 779 (1987); V. V. Grushin and H. Alper, Chem. Rev., 94, 1047 (1994).
    • (1994) Chem. Rev. , vol.94 , pp. 1047
    • Grushin, V.V.1    Alper, H.2
  • 9
    • 2642583738 scopus 로고    scopus 로고
    • note
    • 3 of HMPA at 60 °C for 6 h to give 95% benzonitrile and 2% biphenyl. This should be noted from a synthetic viewpoint.
  • 11
    • 0004029968 scopus 로고
    • Academic Press, New York, Chap. 1
    • 2Mg, see; P. W. Jolly and G. Wilke, "The Organic Chemistry of Nickel," Academic Press, New York (1975), Vol. 2, Chap. 1, pp. 18-21; W. Kaschube, K. R. Porschke, K. Angermund, C. Kruger, and G. Wilke, Chem. Ber., 121, 1921 (1988); An acceleration effect by the complexation of organozinc species in the nickel-catalyzed conjugate addition/aldol reaction was also reported in K. Subburaj and J. Montogomery, J. Am. Chem. Soc., 125, 11210 (2003).
    • (1975) The Organic Chemistry of Nickel , vol.2 , pp. 18-21
    • Jolly, P.W.1    Wilke, G.2
  • 12
    • 84985723178 scopus 로고
    • 2Mg, see; P. W. Jolly and G. Wilke, "The Organic Chemistry of Nickel," Academic Press, New York (1975), Vol. 2, Chap. 1, pp. 18-21; W. Kaschube, K. R. Porschke, K. Angermund, C. Kruger, and G. Wilke, Chem. Ber., 121, 1921 (1988); An acceleration effect by the complexation of organozinc species in the nickel-catalyzed conjugate addition/aldol reaction was also reported in K. Subburaj and J. Montogomery, J. Am. Chem. Soc., 125, 11210 (2003).
    • (1988) Chem. Ber. , vol.121 , pp. 1921
    • Kaschube, W.1    Porschke, K.R.2    Angermund, K.3    Kruger, C.4    Wilke, G.5
  • 13
    • 0042693212 scopus 로고    scopus 로고
    • 2Mg, see; P. W. Jolly and G. Wilke, "The Organic Chemistry of Nickel," Academic Press, New York (1975), Vol. 2, Chap. 1, pp. 18-21; W. Kaschube, K. R. Porschke, K. Angermund, C. Kruger, and G. Wilke, Chem. Ber., 121, 1921 (1988); An acceleration effect by the complexation of organozinc species in the nickel-catalyzed conjugate addition/aldol reaction was also reported in K. Subburaj and J. Montogomery, J. Am. Chem. Soc., 125, 11210 (2003).
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 11210
    • Subburaj, K.1    Montogomery, J.2
  • 16
    • 2642529147 scopus 로고    scopus 로고
    • note
    • 3 the reaction proceeded smoothly to give 84% benzonitrile.
  • 20
    • 0242366043 scopus 로고
    • It is reported that CN migrates between two metals bridging position; W. P. Fehlhammer and M. Fritz, Chem. Rev., 93, 1243 (1993).
    • (1993) Chem. Rev. , vol.93 , pp. 1243
    • Fehlhammer, W.P.1    Fritz, M.2
  • 25
    • 2642541413 scopus 로고
    • Homogeneous catalysis II
    • Am. Chem. Soc.
    • L. Cassar, S. Ferrara, and M. Foa, "Homogeneous Catalysis II," Adv. Chem. Ser. 132, Am. Chem. Soc. (1974), p. 252.
    • (1974) Adv. Chem. Ser. , vol.132 , pp. 252
    • Cassar, L.1    Ferrara, S.2    Foa, M.3


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