Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 12, Pages 5669-5674Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja300416f
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Funding
- U.S. National Science Foundation
- French Agence Nationale de Recherche [ANR-11-BS07-008]
- UHA
- ENSCMu
- CNRS
- Actelion
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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 [C9H19C(CH3)(2)SH]. Rate constants for reaction of the phenylthiyl (PhS center dot) radical with two NHC-boranes have been measured to be similar to 10(8) M-1 s(-1) by laser flash photolysis experiments. An analysis of the available evidence suggests the operation of polarity reversal catalysis.
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