GaCl3-Promoted Addition Reactions of Carbon Nucleophiles to Alkyne.

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  • Kido Yoshiyuki
    Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
  • Arisawa Mieko
    Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
  • Yamaguchi Masahiko
    Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University

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Abstract

GaCl3 promotes addition reactions of carbon nucleophiles to a C-C triple bond. Interaction of alkyne with GaC13 generates a highly reactive electrophile, which aromatic hydrocarbon attacks to give an alkenylated arene. Silylethyne reacts predominantly at the p-position of toluene, while disilylated 1, 3-butadiyne exhibits o-selectivity. The behavior of a silylated 1, 2-propadiene is intermediate between that of the silylethyne and the disilylated 1, 3-butadiyne. In the presence of GaCl3, electrophilic trimerization of silylethyne takes place to give a conjugated hexatriene. In this reaction, silylethyne attacks the GaCl3-activated C-C triple bond. Carbometalation is another interesting addition reaction of an organogallium compound to alkyne. Alkynyldichlorogallium dimerizes in hydrocarbon solvents to give 1, 1-dimetallo-l-buten-3-yne. In the presence of GaCl3, silyl enol ether is ethenylated at the α-carbon atom with trimethylsilylethyne. Treatment of lithium phenoxide with silylethyne in the presence of GaCl3 gives o- (β-silylethenyl) phenol. These reactions involve carbogallation of alkynylgallium, gallium enolate, or gallium phenoxide.

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