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
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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.
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Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Nozaki, K | | | | Aramaki, Y | | | | Yamashita, M | | | | Ueng, SH | | | | Malacria, M | | | | Lacôte, E | | | | Curran, DP | curran@pitt.edu | CURRAN | |
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Date: |
25 August 2010 |
Date Type: |
Publication |
Journal or Publication Title: |
Journal of the American Chemical Society |
Volume: |
132 |
Number: |
33 |
Page Range: |
11449 - 11451 |
DOI or Unique Handle: |
10.1021/ja105277u |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
0002-7863 |
MeSH Headings: |
Borates--chemical synthesis; Borates--chemistry; Crystallography, X-Ray; Free Radicals--chemistry; Ions--chemistry; Models, Molecular; Molecular Structure; Organometallic Compounds--chemistry; Oxidation-Reduction; Stereoisomerism |
PubMed ID: |
20677751 |
Date Deposited: |
08 Feb 2013 20:57 |
Last Modified: |
08 Sep 2021 17:55 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/17270 |
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