Novel Carbon-Carbon Bond Formation through Mizoroki-Heck Type Reaction of Silanols and Organotin Compounds

Abstract

Abstract The reaction of dimethyl(phenyl)silanol with butyl acrylate in the presence of a stoichiometric amount of Pd(OAc)2 or by a combined use of 0.1 molar amount of Pd(OAc)2 and Cu(OAc)2/LiOAc (molar ratio 3/2) gave butyl cinnamate in 76% or 57% yield, respectively. The similar reaction with tributyl(phenyl)tin also proceeded in 77% yield. The organotin compound was shown to react faster than the silanol, although the tin reagent sometimes induced undesirable homo-coupling, while the reaction with silanol did not give such by-product.