An experimental and theoretical study into the facile, homogenous (N-heterocyclic carbene)2-Pd(0) catalyzed diboration of internal and terminal alkynes

Abstract

Pd(ITMe)₂(PhCCPh) acts as a highly reactive pre-catalyst in the unprecedented homogenous catalyzed diboration of terminal and internal alkynes, yielding a number of novel and known syn-1,2-diborylalkenes in a 100% stereoselective manner. DFT calculations suggest that a similar reaction pathway to that proposed for platinum phosphine analogues is followed, and that destabilization of key intermediates by the NHCs is vital to the overall success for the palladium-catalyzed B–B addition to alkynes.