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. 2008 Aug 6;130(31):10082-3.
doi: 10.1021/ja804150k. Epub 2008 Jul 9.

Complexes of borane and N-heterocyclic carbenes: a new class of radical hydrogen atom donor

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Complexes of borane and N-heterocyclic carbenes: a new class of radical hydrogen atom donor

Shau-Hua Ueng et al. J Am Chem Soc. .

Abstract

Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator.

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