Palladium-catalyzed regioselective decarboxylative hydroarylation of alkynyl carboxylic acids with arylboronic acids

Abstract

The synthesis of (deuterated) 1,1-disubstituted alkenes via Pd-catalyzed decarboxylative hydroarylation of alkynyl carboxylic acids with arylboronic acids has been developed. The reaction features excellent regioselectivity, a broad substrate scope and gram-scale synthetic ability and offers a general synthetic method to synthesize 1,1-dideuterio olefins. Preliminary mechanism investigations indicate that 1,1-disubstituted alkenes are formed by hydroarylation of terminal alkynes generated by in situ decarboxylation of alkynyl carboxylic acids.