Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes

Yuanli Xu, Wenlong Chen, Ruihua Pu, Jia Ding, Qing An, Yi Yang (), Weimin Liu () and Zhiwei Zuo ()
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Yuanli Xu: Sichuan University of Science and Engineering
Wenlong Chen: Chinese Academy of Sciences
Ruihua Pu: ShanghaiTech University
Jia Ding: Chinese Academy of Sciences
Qing An: Chinese Academy of Sciences
Yi Yang: Sichuan University of Science and Engineering
Weimin Liu: ShanghaiTech University
Zhiwei Zuo: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract The selective incorporation of a deuterium atom into small molecules with high selectivity is highly valuable for medical and chemical research. Unfortunately, this remains challenging due to the complete deuteration caused by commonly used hydrogen isotope exchange strategies. We report the development of a photocatalytic selective monodeuteration protocol utilizing C–C bond as the unconventional functional handle. The synergistic combination of radical-mediated C–C bond scission and deuterium atom transfer processes enables the effective constructions of benzylic CDH moieties with high selectivity for monodeuteration. The combinational use of a bisphosphonium photocatalyst, thiol catalyst, and CH3OD deuteration agent provides operationally simple conditions for photocatalytic monodeuteration. Moreover, the photoinduced electron transfer process of the bisphosphonium photocatalyst is elucidated through a series of spectroscopy experiments, identifying a peculiar back electron transfer process that can be regulated by subsequent nucleophilic additions.

Date: 2024
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DOI: 10.1038/s41467-024-53728-x

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