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

Ueng, SH and Fensterbank, L and Lacôte, E and Malacria, M and Curran, DP (2011) Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes. Organic and Biomolecular Chemistry, 9 (9). 3415 - 3420. ISSN 1477-0520

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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. © 2011 The Royal Society of Chemistry.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Ueng, SH
Fensterbank, L
Lacôte, E
Malacria, M
Curran, DPcurran@pitt.eduCURRAN
Date: 7 May 2011
Date Type: Publication
Journal or Publication Title: Organic and Biomolecular Chemistry
Volume: 9
Number: 9
Page Range: 3415 - 3420
DOI or Unique Handle: 10.1039/c0ob01075h
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1477-0520
PubMed ID: 21423918
Date Deposited: 08 Feb 2013 21:21
Last Modified: 15 Oct 2017 06:55
URI: http://d-scholarship.pitt.edu/id/eprint/17192

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