title: Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes.
abstract: 1,3-Dimethylimidazol-2-ylidene borane and 2,4-dimethyl-1,2,4-triazol-3-ylidene borane are found to be useful reagents for the reduction of alkyl iodides and bromides bearing nearby electron withdrawing substituents. Signatures of radical chain reactions are seen in many cases, but ionic reductions may also be occurring with some substrates. The reagents are attractive because of their low molecular weight, their availability from inexpensive precursors, and their stability. Separation of the borane products from the target products is readily accomplished either with or without prior regeneration of the borane for later reuse. 2,4-Dimethyl-1,2,4-triazol-3-ylidene borane is versatile because both starting borane and its derived products can be removed by extraction with water.
authors.affiliation: Institut Parisien de Chimie Moléculaire (UMR CNRS 7201) UPMC Univ Paris 06, 4 place Jussieu, C. 229, 75005, Paris, France.
authors.forename: Shau-Hua
authors.initials: SH
authors.lastname: Ueng
authors.forename: Louis
authors.initials: L
authors.lastname: Fensterbank
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Lacôte
authors.forename: Max
authors.initials: M
authors.lastname: Malacria
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran