Zinc-catalyzed C–H alkenylation of quinoline N-oxides with ynones: a new strategy towards quinoline-enol scaffolds

Abstract

A zinc-catalyzed C–H alkenylation of quinoline N-oxides with ynones has been developed to rapidly assemble a broad collection of valuable quinoline-enol organic architectures. Uncommonly, this novel reaction involves C–H functionalization, and N–O, C–C and CC bond cleavage in one operation, and leads exclusively to the formation of an enol rather than a keto product. Application of the enols generated was highlighted by further derivative transformation and preparation of a series of “BODIPY” analogues with high quantum yields (up to 86%).