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Visible light-induced direct α C–H functionalization of alcohols

Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between al...

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Autores principales: Niu, Linbin, Liu, Jiamei, Liang, Xing-An, Wang, Shengchun, Lei, Aiwen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349847/
https://www.ncbi.nlm.nih.gov/pubmed/30692540
http://dx.doi.org/10.1038/s41467-019-08413-9
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author Niu, Linbin
Liu, Jiamei
Liang, Xing-An
Wang, Shengchun
Lei, Aiwen
author_facet Niu, Linbin
Liu, Jiamei
Liang, Xing-An
Wang, Shengchun
Lei, Aiwen
author_sort Niu, Linbin
collection PubMed
description Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective α sp(3) C–H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of α sp(3) C–H alcohols. The observed reactivity may have significant implications for chemical transformations.
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spelling pubmed-63498472019-01-30 Visible light-induced direct α C–H functionalization of alcohols Niu, Linbin Liu, Jiamei Liang, Xing-An Wang, Shengchun Lei, Aiwen Nat Commun Article Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective α sp(3) C–H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of α sp(3) C–H alcohols. The observed reactivity may have significant implications for chemical transformations. Nature Publishing Group UK 2019-01-28 /pmc/articles/PMC6349847/ /pubmed/30692540 http://dx.doi.org/10.1038/s41467-019-08413-9 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Niu, Linbin
Liu, Jiamei
Liang, Xing-An
Wang, Shengchun
Lei, Aiwen
Visible light-induced direct α C–H functionalization of alcohols
title Visible light-induced direct α C–H functionalization of alcohols
title_full Visible light-induced direct α C–H functionalization of alcohols
title_fullStr Visible light-induced direct α C–H functionalization of alcohols
title_full_unstemmed Visible light-induced direct α C–H functionalization of alcohols
title_short Visible light-induced direct α C–H functionalization of alcohols
title_sort visible light-induced direct α c–h functionalization of alcohols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6349847/
https://www.ncbi.nlm.nih.gov/pubmed/30692540
http://dx.doi.org/10.1038/s41467-019-08413-9
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