eprintid: 17192
rev_number: 12
userid: 1418
dir: disk0/00/01/71/92
datestamp: 2013-02-08 21:21:52
lastmod: 2017-10-15 06:55:12
status_changed: 2013-02-08 21:21:52
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Ueng, SH
creators_name: Fensterbank, L
creators_name: Lacôte, E
creators_name: Malacria, M
creators_name: Curran, DP
creators_email: 
creators_email: 
creators_email: 
creators_email: 
creators_email: curran@pitt.edu
creators_id: 
creators_id: 
creators_id: 
creators_id: 
creators_id: CURRAN
title: Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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.
date: 2011-05-07
date_type: published
publication: Organic and Biomolecular Chemistry
volume: 9
number: 9
pagerange: 3415 - 3420
refereed: TRUE
issn: 1477-0520
id_number: 10.1039/c0ob01075h
pmid: 21423918
citation:   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     
document_url: http://d-scholarship-dev.library.pitt.edu/17192/1/licence.txt