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Undue influence: N-heterocyclic carbenes (NHCs) were found to reduce the strength of the B-H bonds of borane by a surprisingly large amount upon the formation of NHC-BH(3) 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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John C. Walton (2009) studied this question.
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