Controllable deuteration of halogenated compounds by photocatalytic D2O splitting

Cuibo Liu, Zhongxin Chen, Chenliang Su (), Xiaoxu Zhao, Qiang Gao, Guo-Hong Ning, Hai Zhu, Wei Tang, Kai Leng, Wei Fu, Bingbing Tian, Xinwen Peng, Jing Li, Qing-Hua Xu, Wu Zhou and Kian Ping Loh ()
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Cuibo Liu: Shenzhen University
Zhongxin Chen: National University of Singapore
Chenliang Su: Shenzhen University
Xiaoxu Zhao: National University of Singapore
Qiang Gao: Shenzhen University
Guo-Hong Ning: National University of Singapore
Hai Zhu: National University of Singapore
Wei Tang: Institute of Materials Research and Engineering
Kai Leng: National University of Singapore
Wei Fu: National University of Singapore
Bingbing Tian: Shenzhen University
Xinwen Peng: National University of Singapore
Jing Li: Shenzhen University
Qing-Hua Xu: Shenzhen University
Wu Zhou: University of Chinese Academy of Sciences
Kian Ping Loh: Shenzhen University

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Deuterium labeling is of great value in organic synthesis and the pharmaceutical industry. However, the state-of-the-art C–H/C–D exchange using noble metal catalysts or strong bases/acids suffers from poor functional group tolerances, poor selectivity and lack of scope for generating molecular complexity. Herein, we demonstrate the deuteration of halides using heavy water as the deuteration reagent and porous CdSe nanosheets as the catalyst. The deuteration mechanism involves the generation of highly active carbon and deuterium radicals via photoinduced electron transfer from CdSe to the substrates, followed by tandem radicals coupling process, which is mechanistically distinct from the traditional methods involving deuterium cations or anions. Our deuteration strategy shows better selectivity and functional group tolerances than current C–H/C–D exchange methods. Extending the synthetic scope, deuterated boronic acids, halides, alkynes, and aldehydes can be used as synthons in Suzuki coupling, Click reaction, C–H bond insertion reaction etc. for the synthesis of complex deuterated molecules.

Date: 2018
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DOI: 10.1038/s41467-017-02551-8

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