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Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

A visible-light-induced nickel-catalyzed cross coupling of alkyl carboxylic acids with N-trifluoroethoxyphthalimide is described. Under purple light irradiation, an α-hydroxytrifluoroethyl radical generated from a photoactive electron donor–acceptor complex between Hantzsch ester and N-trifluoroetho...

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Autores principales: Chen, Feng, Xu, Xiu-Hua, Chen, Zeng-Hao, Chen, Yue, Qing, Feng-Ling
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10509543/
https://www.ncbi.nlm.nih.gov/pubmed/37736392
http://dx.doi.org/10.3762/bjoc.19.98
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author Chen, Feng
Xu, Xiu-Hua
Chen, Zeng-Hao
Chen, Yue
Qing, Feng-Ling
author_facet Chen, Feng
Xu, Xiu-Hua
Chen, Zeng-Hao
Chen, Yue
Qing, Feng-Ling
author_sort Chen, Feng
collection PubMed
description A visible-light-induced nickel-catalyzed cross coupling of alkyl carboxylic acids with N-trifluoroethoxyphthalimide is described. Under purple light irradiation, an α-hydroxytrifluoroethyl radical generated from a photoactive electron donor–acceptor complex between Hantzsch ester and N-trifluoroethoxyphthalimide was subsequently engaged in a nickel-catalyzed coupling reaction with in situ-activated alkyl carboxylic acids. This convenient protocol does not require photocatalysts and metal reductants, providing a straightforward and efficient access to trifluoromethyl alkyl acyloins in good yields with broad substrate compatibility. The complex bioactive molecules were also compatible with this catalytic system to afford the corresponding products.
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spelling pubmed-105095432023-09-21 Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins Chen, Feng Xu, Xiu-Hua Chen, Zeng-Hao Chen, Yue Qing, Feng-Ling Beilstein J Org Chem Full Research Paper A visible-light-induced nickel-catalyzed cross coupling of alkyl carboxylic acids with N-trifluoroethoxyphthalimide is described. Under purple light irradiation, an α-hydroxytrifluoroethyl radical generated from a photoactive electron donor–acceptor complex between Hantzsch ester and N-trifluoroethoxyphthalimide was subsequently engaged in a nickel-catalyzed coupling reaction with in situ-activated alkyl carboxylic acids. This convenient protocol does not require photocatalysts and metal reductants, providing a straightforward and efficient access to trifluoromethyl alkyl acyloins in good yields with broad substrate compatibility. The complex bioactive molecules were also compatible with this catalytic system to afford the corresponding products. Beilstein-Institut 2023-09-11 /pmc/articles/PMC10509543/ /pubmed/37736392 http://dx.doi.org/10.3762/bjoc.19.98 Text en Copyright © 2023, Chen et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Chen, Feng
Xu, Xiu-Hua
Chen, Zeng-Hao
Chen, Yue
Qing, Feng-Ling
Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins
title Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins
title_full Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins
title_fullStr Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins
title_full_unstemmed Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins
title_short Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins
title_sort visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: access to trifluoromethyl alkyl acyloins
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10509543/
https://www.ncbi.nlm.nih.gov/pubmed/37736392
http://dx.doi.org/10.3762/bjoc.19.98
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