Pd(ii)-catalyzed hydroarylations/hydroalkenylations of terminal alkynes: regioselective synthesis of allylic, homoallylic, and 1,3-diene systems

Abstract

A Pd-catalyzed regioselective hydroarylation of terminal alkynes containing a heteroatom has been developed via carbopalladation for the synthesis of allylic ethers, amines, and homoallylic alcohols. Moreover, hydroalkenylation of alkynes produces a variety of stereodefined 1,4-dienes with high regioselectivity. The important features of the present protocol are that it is highly regioselective, operationally rapid, and scalable with a huge substrate scope using only 3 mol% of PdCl₂(PPh₃)₂ catalyst in the presence of a mild base KOAc.