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

The addition of Lewis bases to a cyclic (alkyl)(amino)carbene (CAAC)-supported dihydroboron triflate yields the mixed doubly base-stabilised dihydroboryl cations [(CAAC)BH(2)L](+). Of these, [(CAAC)(2)BH(2)]OTf (OTf = triflate) underwent facile two-electron reduction with KC(8) owing to a 1,2-hydrid...

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Autores principales: Hagspiel, Stephan, Arrowsmith, Merle, Fantuzzi, Felipe, Hermann, Alexander, Paprocki, Valerie, Drescher, Regina, Krummenacher, Ivo, Braunschweig, Holger
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7069503/
https://www.ncbi.nlm.nih.gov/pubmed/32206272
http://dx.doi.org/10.1039/c9sc05026d
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author Hagspiel, Stephan
Arrowsmith, Merle
Fantuzzi, Felipe
Hermann, Alexander
Paprocki, Valerie
Drescher, Regina
Krummenacher, Ivo
Braunschweig, Holger
author_facet Hagspiel, Stephan
Arrowsmith, Merle
Fantuzzi, Felipe
Hermann, Alexander
Paprocki, Valerie
Drescher, Regina
Krummenacher, Ivo
Braunschweig, Holger
author_sort Hagspiel, Stephan
collection PubMed
description The addition of Lewis bases to a cyclic (alkyl)(amino)carbene (CAAC)-supported dihydroboron triflate yields the mixed doubly base-stabilised dihydroboryl cations [(CAAC)BH(2)L](+). Of these, [(CAAC)(2)BH(2)]OTf (OTf = triflate) underwent facile two-electron reduction with KC(8) 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.
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spelling pubmed-70695032020-03-23 Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling Hagspiel, Stephan Arrowsmith, Merle Fantuzzi, Felipe Hermann, Alexander Paprocki, Valerie Drescher, Regina Krummenacher, Ivo Braunschweig, Holger Chem Sci Chemistry The addition of Lewis bases to a cyclic (alkyl)(amino)carbene (CAAC)-supported dihydroboron triflate yields the mixed doubly base-stabilised dihydroboryl cations [(CAAC)BH(2)L](+). Of these, [(CAAC)(2)BH(2)]OTf (OTf = triflate) underwent facile two-electron reduction with KC(8) 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. Royal Society of Chemistry 2019-11-25 /pmc/articles/PMC7069503/ /pubmed/32206272 http://dx.doi.org/10.1039/c9sc05026d Text en This journal is © The Royal Society of Chemistry 2020 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Hagspiel, Stephan
Arrowsmith, Merle
Fantuzzi, Felipe
Hermann, Alexander
Paprocki, Valerie
Drescher, Regina
Krummenacher, Ivo
Braunschweig, Holger
Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling
title Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling
title_full Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling
title_fullStr Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling
title_full_unstemmed Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling
title_short Reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling
title_sort reduction of a dihydroboryl cation to a boryl anion and its air-stable, neutral hydroboryl radical through hydrogen shuttling
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7069503/
https://www.ncbi.nlm.nih.gov/pubmed/32206272
http://dx.doi.org/10.1039/c9sc05026d
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