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Facile and general electrochemical deuteration of unactivated alkyl halides

Herein, a facile and general electroreductive deuteration of unactivated alkyl halides (X = Cl, Br, I) or pseudo-halides (X = OMs) using D(2)O as the economical deuterium source was reported. In addition to primary and secondary alkyl halides, sterically hindered tertiary chlorides also work very we...

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Autores principales: Li, Pengfei, Guo, Chengcheng, Wang, Siyi, Ma, Dengke, Feng, Tian, Wang, Yanwei, Qiu, Youai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9247074/
https://www.ncbi.nlm.nih.gov/pubmed/35773255
http://dx.doi.org/10.1038/s41467-022-31435-9
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author Li, Pengfei
Guo, Chengcheng
Wang, Siyi
Ma, Dengke
Feng, Tian
Wang, Yanwei
Qiu, Youai
author_facet Li, Pengfei
Guo, Chengcheng
Wang, Siyi
Ma, Dengke
Feng, Tian
Wang, Yanwei
Qiu, Youai
author_sort Li, Pengfei
collection PubMed
description Herein, a facile and general electroreductive deuteration of unactivated alkyl halides (X = Cl, Br, I) or pseudo-halides (X = OMs) using D(2)O as the economical deuterium source was reported. In addition to primary and secondary alkyl halides, sterically hindered tertiary chlorides also work very well, affording the target deuterodehalogenated products with excellent efficiency and deuterium incorporation. More than 60 examples are provided, including late-stage dehalogenative deuteration of natural products, pharmaceuticals, and their derivatives, all with excellent deuterium incorporation (up to 99% D), demonstrating the potential utility of the developed method in organic synthesis. Furthermore, the method does not require external catalysts and tolerates high current, showing possible use in industrial applications.
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spelling pubmed-92470742022-07-02 Facile and general electrochemical deuteration of unactivated alkyl halides Li, Pengfei Guo, Chengcheng Wang, Siyi Ma, Dengke Feng, Tian Wang, Yanwei Qiu, Youai Nat Commun Article Herein, a facile and general electroreductive deuteration of unactivated alkyl halides (X = Cl, Br, I) or pseudo-halides (X = OMs) using D(2)O as the economical deuterium source was reported. In addition to primary and secondary alkyl halides, sterically hindered tertiary chlorides also work very well, affording the target deuterodehalogenated products with excellent efficiency and deuterium incorporation. More than 60 examples are provided, including late-stage dehalogenative deuteration of natural products, pharmaceuticals, and their derivatives, all with excellent deuterium incorporation (up to 99% D), demonstrating the potential utility of the developed method in organic synthesis. Furthermore, the method does not require external catalysts and tolerates high current, showing possible use in industrial applications. Nature Publishing Group UK 2022-06-30 /pmc/articles/PMC9247074/ /pubmed/35773255 http://dx.doi.org/10.1038/s41467-022-31435-9 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/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/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Li, Pengfei
Guo, Chengcheng
Wang, Siyi
Ma, Dengke
Feng, Tian
Wang, Yanwei
Qiu, Youai
Facile and general electrochemical deuteration of unactivated alkyl halides
title Facile and general electrochemical deuteration of unactivated alkyl halides
title_full Facile and general electrochemical deuteration of unactivated alkyl halides
title_fullStr Facile and general electrochemical deuteration of unactivated alkyl halides
title_full_unstemmed Facile and general electrochemical deuteration of unactivated alkyl halides
title_short Facile and general electrochemical deuteration of unactivated alkyl halides
title_sort facile and general electrochemical deuteration of unactivated alkyl halides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9247074/
https://www.ncbi.nlm.nih.gov/pubmed/35773255
http://dx.doi.org/10.1038/s41467-022-31435-9
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