Ortho-Vinylation Reaction of Phenols with Ethyne

J Org Chem. 1998 Oct 16;63(21):7298-7305. doi: 10.1021/jo980785f.

Abstract

Phenols were vinylated at the ortho-position with ethyne in the presence of SnCl(4)-Bu(3)N reagent. The reaction was applicable to phenols possessing either electron-donating or electron-withdrawing groups. 2,6-Divinylphenols were synthesized under modified conditions. A reaction mechanism involving carbostannylation of alkynyltin and phenoxytin was discussed.