Boryltrihydroborate: Synthesis, Structure, and Reactivity as a Reductant in Ionic, Organometallic, and Radical Reactions
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- Kyoko Nozaki
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Bunkyo-ku, Tokyo 113-8656, Japan, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA, and UPMC Univ Paris 06, Institut Parisien De Chimie Moléculaire (UMR CNRS 7201), C 229, 4 place Jussieu, 75005 Paris, France
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- Yoshitaka Aramaki
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Bunkyo-ku, Tokyo 113-8656, Japan, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA, and UPMC Univ Paris 06, Institut Parisien De Chimie Moléculaire (UMR CNRS 7201), C 229, 4 place Jussieu, 75005 Paris, France
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- Makoto Yamashita
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Bunkyo-ku, Tokyo 113-8656, Japan, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA, and UPMC Univ Paris 06, Institut Parisien De Chimie Moléculaire (UMR CNRS 7201), C 229, 4 place Jussieu, 75005 Paris, France
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- Shau-Hua Ueng
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Bunkyo-ku, Tokyo 113-8656, Japan, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA, and UPMC Univ Paris 06, Institut Parisien De Chimie Moléculaire (UMR CNRS 7201), C 229, 4 place Jussieu, 75005 Paris, France
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- Max Malacria
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Bunkyo-ku, Tokyo 113-8656, Japan, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA, and UPMC Univ Paris 06, Institut Parisien De Chimie Moléculaire (UMR CNRS 7201), C 229, 4 place Jussieu, 75005 Paris, France
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- Emmanuel Lacôte
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Bunkyo-ku, Tokyo 113-8656, Japan, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA, and UPMC Univ Paris 06, Institut Parisien De Chimie Moléculaire (UMR CNRS 7201), C 229, 4 place Jussieu, 75005 Paris, France
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- Dennis P. Curran
- Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Bunkyo-ku, Tokyo 113-8656, Japan, Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA, and UPMC Univ Paris 06, Institut Parisien De Chimie Moléculaire (UMR CNRS 7201), C 229, 4 place Jussieu, 75005 Paris, France
書誌事項
- 公開日
- 2010-08-02
- DOI
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- 10.1021/ja105277u
- 公開者
- American Chemical Society (ACS)
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説明
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 (11)B, (1)H, and (7)Li 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.
収録刊行物
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- Journal of the American Chemical Society
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Journal of the American Chemical Society 132 (33), 11449-11451, 2010-08-02
American Chemical Society (ACS)
