Selective Syntheses of Z-Alkenes via Photocatalyzed Decarboxylative Coupling of N-Hydroxyphthalimide Esters with Terminal Arylalkynes

A novel, efficient Z-alkene synthesis via photo-catalyzed decarboxylative couplings between terminal aryl alkynes and alkyl N-hydroxyphthalimide (NHPI) esters, which are derived from aliphatic carboxylic acids, is described. A wide range of primary, secondary, and tertiary carboxylates as well as alpha-amino acid and alpha-oxyacid-derived esters were employed as suitable substrates. The mild reaction conditions, broad substrate scope, functional group tolerance, and operational simplicity make this decarboxylative coupling reaction a valuable method in organic syntheses.