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Complexes of Borane and N-heterocyclic Carbenes: a New Class of Radical Hydrogen Atom Donor

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Journal J Am Chem Soc
Specialty Chemistry
Date 2008 Jul 10
PMID 18611014
Citations 29
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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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