Complexes of borane and N-heterocyclic carbenes: a new class of radical hydrogen atom donor |
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| Authors: | Ueng Shau-Hua Brahmi Malika Makhlouf Derat Etienne Fensterbank Louis Lacôte Emmanuel Malacria Max Curran Dennis P |
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| Institution: | Institut de chimie moléculaire (FR 2769), Laboratoire de chimie organique (UMR CNRS 7611), UPMC Univ Paris 06, C. 229, 4 place Jussieu, 75005 Paris, France. |
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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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