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Polarity reversal catalysis in radical reductions of halides by N-heterocyclic carbene boranes

UNSPECIFIED (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 [C9H19C(CH3)2SH]. Rate constants for reaction of the phenylthiyl (PhS•) radical with two NHC-boranes have been measured to be ∼108M-1s-1by 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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Details

Item Type: Article
Status: Published
Date: 28 March 2012
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 134
Number: 12
Page Range: 5669 - 5674
DOI or Unique Handle: 10.1021/ja300416f
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
PubMed ID: 22394128
Date Deposited: 29 Mar 2013 15:52
Last Modified: 05 Jan 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/17951

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