Diamidocarbene Induced B–H Activation: A New Class of Initiator-Free Olefin Hydroboration Reagents

Abstract

Enabled by its enhanced electrophilicity and attenuated nucleophilicity, an N,N′-diamidocarbene (DAC) was found to promote the B–H bond activation of various BH3 complexes and the B–B bond of bis(pinacolato)diboron, constituting the first such examples for an isolable carbene. The resultant DAC-BH3 adducts datively coordinated to Lewis bases (i.e., dimethyl sulfide, trimethylamine, or pyridine) and facilitated the hydroboration of various olefins under mild conditions and in the absence of exogenous initiators.