Copper(ii)-catalyzed protoboration of allenes in aqueous media and open air

Abstract

A method has been developed for the facile Cu(II)-catalyzed protoboration of monosubstituted allenes in aqueous media under atmospheric conditions. The reaction occurs site selectively, favoring internal alkene protoboration to afford 1,1-disubstituted vinylboronic acid derivatives (up to 93 : 7) with modest to good yields. The method has been applied to a variety of phenylallene derivatives as well as alkyl-substituted allenes.