Copper-catalyzed enantioselective arylboronation of activated alkenes leading to chiral 3,3′-disubstituted oxindoles

Abstract

We here describe the first example of copper-catalyzed enantioselective arylboronation of activated alkenes with bis(pinacolato)diboron (B₂Pin₂) for the synthesis of chiral 3,3′-disubstituted oxindoles. This method enables the formation of a C(sp²)–C(sp³) bond and a C(sp³)–B bond in a single operation, and provides a new asymmetric synthetic toolbox to incorporate boron atoms into heterocycle motifs using inexpensive copper catalysis.