Doubly Regioselective C-H Hydroarylation of Unsymmetrical Alkynes Using Carboxylates as Deciduous Directing Groups.

A catalyst system composed of [(C6Me6)RuCl2]2, potassium carbonate/guanidine carbonate, and mesitoic acid efficiently promotes the doubly regioselective C-H hydroarylation of unsymmetrical alkynes. The process involves carboxylate-directed ortho-C-H bond activation followed by regioselective addition to the alkyne C-C triple bond with concerted decarboxylation. This action of the carboxylate as a deciduous directing group ensures exclusive monovinylation with high selectivity for the (E)-1,2-diarylalkene.