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Y. Kido, S. Yoshimura, M. Yamaguchi, and T. Uchimaru
[Bull. Chem. Soc. Jpn., Vol. 72, No. 7, pp. 1445-1458, 1999]
In the presence of GaCl3, silylethyne reacted electro-philically with aromatic hydrocarbons to give beta-silylethenylated arenes. High reactivity of the intermediate was demonstrated by the rapid reaction rate at -78C using close to the equimolar amount of the substrates. ipso-Substitution reaction took place with 1,2,3-trimethoxybenzen. Ab initio calculations suggested that the reaction should proceed via cationic species generated by the interaction of GaCl3 and silylethyne, which gave a reasonable interpretation toward the regioselectivity of the reaction. Structures and properties of postulated cationic intermediates are discussed.
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