Palladium-catalysed 1,4-arylation/alkylation of buta-1,3-diene with halogenoarenes and stabilised anions

Abstract

In the presence of a palladium–phosphine catalyst, buta-1,3-diene reacts with halogenoarenes and ^–CH(CN)₂ to give 1,4-arylation/alkylation products of the diene, ArCH₂CHCHCH₂C(Ar)(CN)₂(6), in moderate yields. In this reaction, two carbon–carbon bonds are built up from three components by a tandem insertion/coupling reaction in one catalytic cycle. Stabilised anions such as ^–CH(CN)CO₂Me and ^–CH(CO₂Et)₂ similarly yield 1,4-arylation/alkylation products.