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Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single‐electron reduction of an α‐boryl radical intermediate to the correspon...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838549/ https://www.ncbi.nlm.nih.gov/pubmed/29316095 http://dx.doi.org/10.1002/anie.201712186 |
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author | Noble, Adam Mega, Riccardo S. Pflästerer, Daniel Myers, Eddie L. Aggarwal, Varinder K. |
author_facet | Noble, Adam Mega, Riccardo S. Pflästerer, Daniel Myers, Eddie L. Aggarwal, Varinder K. |
author_sort | Noble, Adam |
collection | PubMed |
description | The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single‐electron reduction of an α‐boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α‐amino, α‐oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron‐containing molecules of potential biological importance. |
format | Online Article Text |
id | pubmed-5838549 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-58385492018-03-12 Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters Noble, Adam Mega, Riccardo S. Pflästerer, Daniel Myers, Eddie L. Aggarwal, Varinder K. Angew Chem Int Ed Engl Communications The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single‐electron reduction of an α‐boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α‐amino, α‐oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron‐containing molecules of potential biological importance. John Wiley and Sons Inc. 2018-01-26 2018-02-19 /pmc/articles/PMC5838549/ /pubmed/29316095 http://dx.doi.org/10.1002/anie.201712186 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Noble, Adam Mega, Riccardo S. Pflästerer, Daniel Myers, Eddie L. Aggarwal, Varinder K. Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters |
title | Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters |
title_full | Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters |
title_fullStr | Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters |
title_full_unstemmed | Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters |
title_short | Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters |
title_sort | visible‐light‐mediated decarboxylative radical additions to vinyl boronic esters: rapid access to γ‐amino boronic esters |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838549/ https://www.ncbi.nlm.nih.gov/pubmed/29316095 http://dx.doi.org/10.1002/anie.201712186 |
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