Phosphine-Catalyzed Intermolecular Dienylation of Alkynoate with <i>para</i>-Quinone Methides

Abstract

An interesting remote δ-C 1,6-addition and an isomerization cascade reaction for phosphine-catalyzed activated alkynes have been disclosed. The products featuring a functional diene and a 1,1-diaryl methyl motif have been obtained in moderate to good yields (30-86%) by applying <i>para</i>-quinone methides (<i>p-</i>QMs) and δ-substituted alkynoate with tributylphosphine (P^<i>n</i>Bu₃) catalysis, along with high regioselectivity and stereoselectivity (dr > 20:1). The wide scope of compatible substrates (35 examples), such as indolyl, oxindolyl, ester, and cinnamyl, expand the utility of this methodology. A plausible mechanism and some applications of it have also been presented.