%0 Journal Article
%@ 1523-7060
%A Horn, M
%A Mayr, H
%A Lacôte, E
%A Merling, E
%A Deaner, J
%A Wells, S
%A McFadden, T
%A Curran, DP
%D 2012
%F pittir:17796
%J Organic Letters
%N 1
%P 82 - 85
%T N-heterocyclic carbene boranes are good hydride donors
%U http://d-scholarship-dev.library.pitt.edu/17796/
%V 14
%X 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.