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Boryltrihydroborate: Synthesis, structure, and reactivity as a reductant in ionic, organometallic, and radical reactions

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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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
Status: Published
CreatorsEmailPitt UsernameORCID
Nozaki, K
Aramaki, Y
Yamashita, M
Ueng, SH
Malacria, M
Lacôte, E
Curran, DPcurran@pitt.eduCURRAN
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: 22 Jun 2021 12:56


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