Ni/Cu-Catalyzed Decarboxylative Addition of Alkynoic Acids to Terminal Alkynes for the Synthesis of gem-1,3-Enynes

The synthesis of gem-1,3-enynes via Ni/Cu-catalyzed decarboxylative addition of alkynoic acids to terminal alkynes has been developed. It was found that the decarboxylation of an alkynoic acid led predominantly to gem-1,3-enynes instead of 1,3-diynes, which have been known to be formed through the coupling of terminal alkynes. A variety of gem-1,3-enynes were obtained in good yields. This catalytic system exhibited excellent regioselectivity and high functional group tolerance.