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Issue 9, 2011
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Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes

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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.

Graphical abstract: Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes

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Publication details

The article was received on 24 Nov 2010, accepted on 25 Jan 2011 and first published on 26 Jan 2011


Article type: Paper
DOI: 10.1039/C0OB01075H
Citation: Org. Biomol. Chem., 2011,9, 3415-3420
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    Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes

    S. Ueng, L. Fensterbank, E. Lacôte, M. Malacria and D. P. Curran, Org. Biomol. Chem., 2011, 9, 3415
    DOI: 10.1039/C0OB01075H

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