Pan, X and Lacôte, E and Lalevée, J and Curran, DP
(2012)
Polarity reversal catalysis in radical reductions of halides by N-heterocyclic carbene boranes.
Journal of the American Chemical Society, 134 (12).
5669 - 5674.
ISSN 0002-7863
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Abstract
Otherwise sluggish or completely ineffective radical reductions of alkyl and aryl halides by N-heterocyclic carbene boranes (NHC-boranes) are catalyzed by thiols. Reductions and reductive cyclizations with readily available 1,3-dimethylimidazol-2-ylidene borane and a water-soluble triazole relative are catalyzed by thiophenol and tert-dodecanethiol [C 9H 19C(CH 3) 2SH]. Rate constants for reaction of the phenylthiyl (PhS•) radical with two NHC-boranes have been measured to be ∼10 8 M -1 s -1 by laser flash photolysis experiments. An analysis of the available evidence suggests the operation of polarity reversal catalysis. © 2012 American Chemical Society.
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