Carbonyls as Potential Alkenyl Carbanions for Deoxygenative Cross-Coupling with Alkyl Electrophiles

Abstract

The example of carbonyls as alkenyl carbanions for deoxygenative cross-coupling with alkyl electrophiles has been developed, facilitating the efficient synthesis of alkenes and enabling carbonyl 1,2-transposition alkylation. This protocol features a one-pot three-step synthesis, compatibility with diverse functional groups, mild reaction conditions, and latestage functionalization of biomolecules. Initial experiments and DFT mechanistic studies suggest that the in-situ generated alkenyl boronic esters play a crucial role as intermediates in this reaction, and this transformation involves C-O bond borylation and the Suzuki coupling reaction under transition metal-free conditions.