Controllable deuteration of halogenated compounds by photocatalytic D2O splitting

Liu, Cuibo; Chen, Zhongxin; Su, Chenliang; Zhao, Xiaoxu; Gao, Qiang; Ning, Guo-Hong; Zhu, Hai; Tang, Wei; Leng, Kai; Fu, Wei; Tian, Bingbing; Peng, Xinwen; Li, Jing; Xu, Qing-Hua; Zhou, Wu; Loh, Kian Ping

doi:10.1038/s41467-017-02551-8

Controllable deuteration of halogenated compounds by photocatalytic D2O splitting

Journal Article · Mon Jan 08 00:00:00 EST 2018 · Nature Communications

DOI:https://doi.org/10.1038/s41467-017-02551-8· OSTI ID:1624069

Liu, Cuibo ^[1]; Chen, Zhongxin ^[2]; ^[3]; ^[2]; ^[3]; Ning, Guo-Hong ^[4]; Zhu, Hai ^[4]; Tang, Wei ^[4]; Leng, Kai ^[4]; Fu, Wei ^[4]; ^[3]; Peng, Xinwen ^[4]; ^[3]; Xu, Qing-Hua ^[3]; Zhou, Wu ^[5]; Loh, Kian Ping ^[3]

Shenzhen Univ., Shen Zhen (China). College of Optoelectronic Engineering. Engineering Technology Research Center for 2D Materials Information Functional Devices and Systems of Guangdong Province. SZU-NUS Collaborative Center and International Collaborative Laboratory of 2D Materials for Optoelectronic Science & Technology; National Univ. of Singapore (Singapore). Dept. of Chemistry and Centre for Advanced 2D Materials (CA2DM); DOE/OSTI
National Univ. of Singapore (Singapore). Dept. of Chemistry and Centre for Advanced 2D Materials (CA2DM); National Univ. of Singapore (Singapore). NUS Graduate School for Integrative Sciences and Engineering. Centre for Life Sciences
Shenzhen Univ., Shen Zhen (China). College of Optoelectronic Engineering. Engineering Technology Research Center for 2D Materials Information Functional Devices and Systems of Guangdong Province. SZU-NUS Collaborative Center and International Collaborative Laboratory of 2D Materials for Optoelectronic Science & Technology; National Univ. of Singapore (Singapore). Dept. of Chemistry and Centre for Advanced 2D Materials (CA2DM)
National Univ. of Singapore (Singapore). Dept. of Chemistry and Centre for Advanced 2D Materials (CA2DM)
Chinese Academy of Sciences (CAS), Beijing (China). CAS Key Laboratory of Vacuum Physics. School of Physical Sciences

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.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1624069

Journal Information:: Nature Communications, Journal Name: Nature Communications Journal Issue: 1 Vol. 9; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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