Radical-polar crossover reactions: oxidative coupling of 1,3-dioxolanes with electron-deficient alkenes and vinylarenes based on a radical addition and Kornblum-DeLaMare rearrangement.

Abstract

A new radical-polar crossover reaction has been developed involving the combination of a tandem radical reaction and Kornblum-DeLaMare rearrangement in a one-pot process. This simple methodology allows for the construction of polyfunctionalized carbonyl compounds via the oxidative coupling of 1,3-dioxolanes with electron-deficient alkenes and vinylarenes in the presence of Co(salen) and TBHP under mild conditions. This reaction also exhibited high functional group tolerance, wide substrate scope, and operational simplicity.