Conceptual approach to the synthesis of symmetrical 1,3-diynes from β-bromo vinyl carboxylic acids

A conceptual route has been developed for the synthesis of 1,3-diyne from beta-bromo vinyl carboxylic acids. The reaction of the beta-bromo vinyl carboxylic acid with palladium catalyst is conceptually similar to the decomposition of 2-diazoniumbenzoic acid to benzyne. In the presence of palladium catalyst, the beta-bromo vinyl carboxylic acid undergoes a fragmentation to generate terminal alkyne. The terminal alkyne undergoes dimerisation in the presence of palladium catalysts to produce the product 1,3-diyne.