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A highly selective decarboxylative deuteration of carboxylic acids

In this paper, we report a mild and practical method for precise deuteration of aliphatic carboxylic acids by synergistic photoredox and HAT catalysis. The reaction delivers excellent D-incorporation (up to 99%) at predicted sites even in substrates bearing reactive C–H bonds or versatile functional...

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Detalles Bibliográficos
Autores principales: Li, Nian, Ning, Yunyun, Wu, Xiaopeng, Xie, Jin, Li, Weipeng, Zhu, Chengjian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179560/
https://www.ncbi.nlm.nih.gov/pubmed/34163771
http://dx.doi.org/10.1039/d1sc00528f
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author Li, Nian
Ning, Yunyun
Wu, Xiaopeng
Xie, Jin
Li, Weipeng
Zhu, Chengjian
author_facet Li, Nian
Ning, Yunyun
Wu, Xiaopeng
Xie, Jin
Li, Weipeng
Zhu, Chengjian
author_sort Li, Nian
collection PubMed
description In this paper, we report a mild and practical method for precise deuteration of aliphatic carboxylic acids by synergistic photoredox and HAT catalysis. The reaction delivers excellent D-incorporation (up to 99%) at predicted sites even in substrates bearing reactive C–H bonds or versatile functional groups. The use of a recirculation reactor with a peristaltic pump supports a scalable preparative ability (up to 50 mmol) under very mild reaction conditions. The practical and precise deuteration of readily available complex carboxylic acids makes this protocol promising for the preparation of deuterium-labelled compounds.
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spelling pubmed-81795602021-06-22 A highly selective decarboxylative deuteration of carboxylic acids Li, Nian Ning, Yunyun Wu, Xiaopeng Xie, Jin Li, Weipeng Zhu, Chengjian Chem Sci Chemistry In this paper, we report a mild and practical method for precise deuteration of aliphatic carboxylic acids by synergistic photoredox and HAT catalysis. The reaction delivers excellent D-incorporation (up to 99%) at predicted sites even in substrates bearing reactive C–H bonds or versatile functional groups. The use of a recirculation reactor with a peristaltic pump supports a scalable preparative ability (up to 50 mmol) under very mild reaction conditions. The practical and precise deuteration of readily available complex carboxylic acids makes this protocol promising for the preparation of deuterium-labelled compounds. The Royal Society of Chemistry 2021-03-03 /pmc/articles/PMC8179560/ /pubmed/34163771 http://dx.doi.org/10.1039/d1sc00528f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Li, Nian
Ning, Yunyun
Wu, Xiaopeng
Xie, Jin
Li, Weipeng
Zhu, Chengjian
A highly selective decarboxylative deuteration of carboxylic acids
title A highly selective decarboxylative deuteration of carboxylic acids
title_full A highly selective decarboxylative deuteration of carboxylic acids
title_fullStr A highly selective decarboxylative deuteration of carboxylic acids
title_full_unstemmed A highly selective decarboxylative deuteration of carboxylic acids
title_short A highly selective decarboxylative deuteration of carboxylic acids
title_sort highly selective decarboxylative deuteration of carboxylic acids
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179560/
https://www.ncbi.nlm.nih.gov/pubmed/34163771
http://dx.doi.org/10.1039/d1sc00528f
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