Catalytic Boracarboxylation of Alkynes with Diborane and Carbon Dioxide by an N-Heterocyclic Carbene Copper Catalyst

By the use of an N-heterocyclic carbene copper(I) complex as a catalyst, the boracarboxylation of various alkynes (e.g., diaryl alkynes, aryl/alkyl alkynes, and phenylacetylene) with a diborane compound and carbon dioxide has been achieved for the first time, affording the alpha,beta-unsaturated beta-boralactone derivatives regio- and stereoselectively via a borylcupration/carboxylation cascade. Some important reaction intermediates were isolated and structurally characterized to clarify the reaction mechanism.