Aromatic <i>β</i>-Silylethenylation Reactions via Organogallium Compounds

Abstract

Abstract In the presence of GaCl3, silylethyne reacted electrophilically with aromatic hydrocarbons to give β-silylethenylated arenes. The reaction proceeded via cationic species generated by the interaction of GaCl3 and silylethyne. High reactivity of the intermediate was demonstrated by the rapid reaction rate at −78 °C using close to the equimolar amount of the substrates. ipso-Substitution reaction took place with 1,2,3-trimethoxybenzene. Structures and properties of several organogallium compounds involved in the reactions are discussed.