@article{pittir17796, volume = {14}, number = {1}, month = {January}, author = {M Horn and H Mayr and E Lac{\^o}te and E Merling and J Deaner and S Wells and T McFadden and DP Curran}, title = {N-heterocyclic carbene boranes are good hydride donors}, journal = {Organic Letters}, pages = {82 -- 85}, year = {2012}, url = {http://d-scholarship-dev.library.pitt.edu/17796/}, abstract = {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. {\copyright} 2011 American Chemical Society.} }