Facile and general electrochemical deuteration of unactivated alkyl halides

Pengfei Li, Chengcheng Guo, Siyi Wang, Dengke Ma, Tian Feng, Yanwei Wang and Youai Qiu ()
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Pengfei Li: Nankai University
Chengcheng Guo: Nankai University
Siyi Wang: Nankai University
Dengke Ma: Nankai University
Tian Feng: Nankai University
Yanwei Wang: Nankai University
Youai Qiu: Nankai University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Herein, a facile and general electroreductive deuteration of unactivated alkyl halides (X = Cl, Br, I) or pseudo-halides (X = OMs) using D2O 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.

Date: 2022
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DOI: 10.1038/s41467-022-31435-9

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