Undue influence: N-heterocyclic carbenes (NHCs) were found to reduce the strength of the BH bonds of borane by a surprisingly large amount upon the formation of NHC–BH3 complexes. This property was exploited in the development of a suite of NHC–borane complexes for the reduction of xanthates in radical-mediated Barton–McCombie-type deoxygenation reactions (see scheme). AIBN=azobisisobutyronitrile, Bn=benzyl.
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