TY - JOUR ID - pittir17796 UR - http://d-scholarship-dev.library.pitt.edu/17796/ IS - 1 A1 - Horn, M A1 - Mayr, H A1 - Lacôte, E A1 - Merling, E A1 - Deaner, J A1 - Wells, S A1 - McFadden, T A1 - Curran, DP Y1 - 2012/01/06/ N2 - The nucleophilicity parameters (N) of 1,3-bis(2,6-diisopropylphenyl) imidazol-2-ylidene borane and 1,3-dimethylimidazol-2-ylidene borane are 9.55 and 11.88. This places N-heterocyclic carbene boranes (NHC-boranes) among the most nucleophilic classes of neutral hydride donors. Reductions of highly electron-poor C=N and C=C bonds provide hydrogenation products along with new, stable borylated products. The results suggest that NHC-boranes have considerable untapped potential as neutral organic reductants. © 2011 American Chemical Society. JF - Organic Letters VL - 14 SN - 1523-7060 TI - N-heterocyclic carbene boranes are good hydride donors SP - 82 AV - public EP - 85 ER -