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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Bibliographic Details
Published in:Nature communications 2022-06, Vol.13 (1), p.3774-3774, Article 3774
Main Authors: Li, Pengfei, Guo, Chengcheng, Wang, Siyi, Ma, Dengke, Feng, Tian, Wang, Yanwei, Qiu, Youai
Format: Article
Language:English
Subjects:
140/131
639/638/161/886
639/638/224/685
639/638/403/933
639/638/77/886
Carbon
Catalysts
Deuteration
Deuterium
Electrochemistry
Electrolytes
Halides
Heavy water
Humanities and Social Sciences
Industrial applications
multidisciplinary
Natural products
Organic chemistry
Pharmaceuticals
Science
Science (multidisciplinary)
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Summary: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. Deuterium-labelled compounds are useful for mechanistic studies and pharmaceutical science, but syntheses are not trivial. Here, the authors report deuteration of unactivated alkyl (pseudo)halides driven by electrochemical force, using deuterium oxide as the source of the isotope.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-022-31435-9