Nucleophilic addition and substitution at coordinatively saturated boron by facile 1,2-hydrogen shuttling onto a carbene donor.

ABSTRACT: The reaction of [(cAAC^Me)BH₃] (cAAC^Me = 1-(2,6-ⁱPr₂C₆H₃)-3,3,5,5-tetramethylpyrrolidin-2-ylidene) with a range of organolithium compounds led to the exclusive formation of the corresponding (dihydro)organoborates, Li⁺[(cAAC^MeH)BH₂R]^- (R = sp³-, sp²-, or sp-hybridised organic substituent), by migration of one boron-bound hydrogen atom to the adjacent carbene carbon of the cAAC ligand. A subsequent deprotonation/salt metathesis reaction with Me₃SiCl or spontaneous LiH elimination yielded the neutral cAAC-supported mono(organo)boranes, [(cAAC^Me)BH₂R]. Similarly the reaction of [(cAAC^Me)BH₃] with a

SUBMITTER: Auerhammer D 

PROVIDER: S-EPMC5637459 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature