eprintid: 17270
rev_number: 24
userid: 1418
dir: disk0/00/01/72/70
datestamp: 2013-02-08 20:57:41
lastmod: 2021-09-08 17:55:08
status_changed: 2013-02-08 20:57:41
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Nozaki, K
creators_name: Aramaki, Y
creators_name: Yamashita, M
creators_name: Ueng, SH
creators_name: Malacria, M
creators_name: Lacôte, E
creators_name: Curran, DP
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creators_email: curran@pitt.edu
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creators_id: CURRAN
title: Boryltrihydroborate: Synthesis, structure, and reactivity as a reductant in ionic, organometallic, and radical reactions
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: Reaction of lithium 1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2- diazaborol-2-ide with borane·THF provides the first boryl-substituted borohydride: lithium [1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2- diazaborol-2-yl]trihydroborate. The compound is fully characterized by 11B, 1H, and 7Li NMR spectra and other means, and these data are compared to neutral and anionic benchmark compounds. The compound crystallizes as a dimer complexed to four THF molecules. The dimer lacks the bridging B-H bonds seen in neutral boranes and is instead held together by ionic Li - -HB interactions. A preliminary scan of reactions with several iodides shows that the compound participates in an ionic reduction (with a primary-alkyl iodide), an organometallic reduction (Pd-catalyzed with an aryl iodide), and a radical reduction (AIBN-initiated with a sugar-derived iodide). Accordingly the new borylborohydride class may share properties of both traditional borohydrides and isoelectronic N-heterocyclic carbene boranes. © 2010 American Chemical Society.
date: 2010-08-25
date_type: published
publication: Journal of the American Chemical Society
volume: 132
number: 33
pagerange: 11449 - 11451
refereed: TRUE
issn: 0002-7863
id_number: 10.1021/ja105277u
pmid: 20677751
mesh_headings: Borates--chemical synthesis
mesh_headings: Borates--chemistry
mesh_headings: Crystallography, X-Ray
mesh_headings: Free Radicals--chemistry
mesh_headings: Ions--chemistry
mesh_headings: Models, Molecular
mesh_headings: Molecular Structure
mesh_headings: Organometallic Compounds--chemistry
mesh_headings: Oxidation-Reduction
mesh_headings: Stereoisomerism
chemical_names: Borates
chemical_names: Free Radicals
chemical_names: Ions
chemical_names: Organometallic Compounds
citation:   Nozaki, K and Aramaki, Y and Yamashita, M and Ueng, SH and Malacria, M and Lacôte, E and Curran, DP  (2010) Boryltrihydroborate: Synthesis, structure, and reactivity as a reductant in ionic, organometallic, and radical reactions.  Journal of the American Chemical Society, 132 (33).  11449 - 11451.  ISSN 0002-7863     
document_url: http://d-scholarship-dev.library.pitt.edu/17270/1/licence.txt