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Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling

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Abstract

The addition of Lewis bases to a cyclic (alkyl)(amino)carbene (CAAC)-supported dihydroboron triflate yields the mixed doubly base-stabilised dihydroboryl cations [(CAAC)BH2L]+. Of these, [(CAAC)2BH2]OTf (OTf = triflate) underwent facile two-electron reduction with KC8 owing to a 1,2-hydride migration from boron to the carbene carbon to yield a stable hydroboryl anion. One-electron oxidation of the latter yielded the first neutral hydroboryl radical, which is bench-stable in the solid state.

Graphical abstract: Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling

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Publication details

The article was received on 07 Oct 2019, accepted on 23 Nov 2019 and first published on 25 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC05026D
Chem. Sci., 2020, Advance Article
  • Open access: Creative Commons BY license
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    Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling

    S. Hagspiel, M. Arrowsmith, F. Fantuzzi, A. Hermann, V. Paprocki, R. Drescher, I. Krummenacher and H. Braunschweig, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC05026D

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