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Issue 2, 2020
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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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Article information


Submitted
07 Oct 2019
Accepted
23 Nov 2019
First published
25 Nov 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 551-555
Article type
Edge Article

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, 11, 551
DOI: 10.1039/C9SC05026D

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