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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...

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Autores principales: Huang, Hua, Dai, Qing-Song, Leng, Hai-Jun, Li, Qing-Zhu, Yang, Si-Lin, Tao, Ying-Mao, Zhang, Xiang, Qi, Ting, Li, Jun-Long
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
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.
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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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