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Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis
The Suzuki–Miyaura cross-coupling of C(sp(3))-hybridised boronic compounds still remains a challenging task, thereby hindering the broad application of alkyl boron substrates in carbon–carbon bond-forming reactions. Herein, we developed an NHC/photoredox dual catalytic cross-coupling of alkyl triflu...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8890133/ https://www.ncbi.nlm.nih.gov/pubmed/35356672 http://dx.doi.org/10.1039/d1sc06102j |
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author | Huang, Hua Dai, Qing-Song Leng, Hai-Jun Li, Qing-Zhu Yang, Si-Lin Tao, Ying-Mao Zhang, Xiang Qi, Ting Li, Jun-Long |
author_facet | Huang, Hua Dai, Qing-Song Leng, Hai-Jun Li, Qing-Zhu Yang, Si-Lin Tao, Ying-Mao Zhang, Xiang Qi, Ting Li, Jun-Long |
author_sort | Huang, Hua |
collection | PubMed |
description | The Suzuki–Miyaura cross-coupling of C(sp(3))-hybridised boronic compounds still remains a challenging task, thereby hindering the broad application of alkyl boron substrates in carbon–carbon bond-forming reactions. Herein, we developed an NHC/photoredox dual catalytic cross-coupling of alkyl trifluoroborates with acid fluorides, providing an alternative solution to the classical acylative Suzuki coupling chemistry. With this protocol, various ketones could be rapidly synthesised from readily available materials under mild conditions. Preliminary mechanistic studies shed light on the unique radical reaction mechanism. |
format | Online Article Text |
id | pubmed-8890133 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-88901332022-03-29 Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis Huang, Hua Dai, Qing-Song Leng, Hai-Jun Li, Qing-Zhu Yang, Si-Lin Tao, Ying-Mao Zhang, Xiang Qi, Ting Li, Jun-Long Chem Sci Chemistry The Suzuki–Miyaura cross-coupling of C(sp(3))-hybridised boronic compounds still remains a challenging task, thereby hindering the broad application of alkyl boron substrates in carbon–carbon bond-forming reactions. Herein, we developed an NHC/photoredox dual catalytic cross-coupling of alkyl trifluoroborates with acid fluorides, providing an alternative solution to the classical acylative Suzuki coupling chemistry. With this protocol, various ketones could be rapidly synthesised from readily available materials under mild conditions. Preliminary mechanistic studies shed light on the unique radical reaction mechanism. The Royal Society of Chemistry 2022-01-21 /pmc/articles/PMC8890133/ /pubmed/35356672 http://dx.doi.org/10.1039/d1sc06102j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Huang, Hua Dai, Qing-Song Leng, Hai-Jun Li, Qing-Zhu Yang, Si-Lin Tao, Ying-Mao Zhang, Xiang Qi, Ting Li, Jun-Long Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis |
title | Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis |
title_full | Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis |
title_fullStr | Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis |
title_full_unstemmed | Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis |
title_short | Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis |
title_sort | suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by nhc/photoredox dual catalysis |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8890133/ https://www.ncbi.nlm.nih.gov/pubmed/35356672 http://dx.doi.org/10.1039/d1sc06102j |
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