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A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters
We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alk...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5708277/ https://www.ncbi.nlm.nih.gov/pubmed/29024307 http://dx.doi.org/10.1002/anie.201709690 |
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author | Lima, Fabio Sharma, Upendra K. Grunenberg, Lars Saha, Debasmita Johannsen, Sandra Sedelmeier, Joerg Van der Eycken, Erik V. Ley, Steven V. |
author_facet | Lima, Fabio Sharma, Upendra K. Grunenberg, Lars Saha, Debasmita Johannsen, Sandra Sedelmeier, Joerg Van der Eycken, Erik V. Ley, Steven V. |
author_sort | Lima, Fabio |
collection | PubMed |
description | We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron‐deficient olefins via radical addition to efficiently form C−C coupled products in a redox‐neutral fashion. The Lewis base catalyst was shown to form a redox‐active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution. |
format | Online Article Text |
id | pubmed-5708277 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-57082772017-12-04 A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters Lima, Fabio Sharma, Upendra K. Grunenberg, Lars Saha, Debasmita Johannsen, Sandra Sedelmeier, Joerg Van der Eycken, Erik V. Ley, Steven V. Angew Chem Int Ed Engl Communications We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron‐deficient olefins via radical addition to efficiently form C−C coupled products in a redox‐neutral fashion. The Lewis base catalyst was shown to form a redox‐active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution. John Wiley and Sons Inc. 2017-10-24 2017-11-20 /pmc/articles/PMC5708277/ /pubmed/29024307 http://dx.doi.org/10.1002/anie.201709690 Text en © 2017 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 Lima, Fabio Sharma, Upendra K. Grunenberg, Lars Saha, Debasmita Johannsen, Sandra Sedelmeier, Joerg Van der Eycken, Erik V. Ley, Steven V. A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters |
title | A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters |
title_full | A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters |
title_fullStr | A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters |
title_full_unstemmed | A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters |
title_short | A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters |
title_sort | lewis base catalysis approach for the photoredox activation of boronic acids and esters |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5708277/ https://www.ncbi.nlm.nih.gov/pubmed/29024307 http://dx.doi.org/10.1002/anie.201709690 |
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