Palladium‐Catalyzed Decarboxylative Homodimerization of Propiolic Acids: Synthesis of 1,3‐Enynes

Abstract

The 1,3‐enyne product was obtained as a result of a decarboxylative homodimerization reaction when a variety aryl propiolic acids were reacted in the presence of Pd(TFA)2/i‐PrPPh2 and K2CO3. It was found that aryl propiolic acids bearing an electrondonating substituent provided the desired product; however, aryl propiolic acids an bearing electron‐withdrawing substituent did not give the desired product.

Recent advances in catalytic decarboxylative transformations of carboxylic acid groups attached to a non-aromatic sp2or sp carbon

“…Subsequently, the strategy was extended to provide gem -1,3-enynes 185 via a twofold decarboxylative homodimerization process of alkynoic acids (Scheme 59). 76…”

“…Subsequently, the strategy was extended to provide gem-1,3-enynes 185 via a twofold decarboxylative homodimerization process of alkynoic acids (Scheme 59). 76 Xie et al reported an interesting approach for the synthesis of 1,4-enyne 188 motifs in high efficiency via the decarboxylative cross-coupling of alkynoic acids with allylic alcohols 186 or 187 (Scheme 60). 77 The reaction proceeds via the calciumpromoted dehydroxylation of allylic alcohols (C-OH cleavage) linked with consecutive decarboxylation and palladium-catalyzed allyl-alkynyl coupling processes.…”