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

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.