Please use this identifier to cite or link to this item: https://doi.org/10.1038/s41467-017-02551-8
Title: Controllable deuteration of halogenated compounds by photocatalytic D2O splitting
Authors: Liu C. 
Chen Z. 
Su C. 
Zhao X. 
Gao Q. 
Ning G.-H. 
Zhu H.
Tang W.
Leng K. 
Fu W. 
Tian B. 
Peng X.
Li J. 
Xu Q.-H. 
Zhou W.
Loh K.P. 
Keywords: activated carbon
aldehyde derivative
alkyne derivative
anion
boronic acid derivative
cadmium selenide
cation
deuterium oxide
halide
nanosheet
carbon
catalysis
catalyst
chemical bonding
deuterium
halide
pharmaceutical industry
porous medium
Article
chemical modification
chemical structure
electron transport
photocatalysis
reaction analysis
Suzuki reaction
Issue Date: 2018
Publisher: Nature Publishing Group
Citation: Liu C., Chen Z., Su C., Zhao X., Gao Q., Ning G.-H., Zhu H., Tang W., Leng K., Fu W., Tian B., Peng X., Li J., Xu Q.-H., Zhou W., Loh K.P. (2018). Controllable deuteration of halogenated compounds by photocatalytic D2O splitting. Nature Communications 9 (1) : 80. ScholarBank@NUS Repository. https://doi.org/10.1038/s41467-017-02551-8
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. © 2017 The Author(s).
Source Title: Nature Communications
URI: https://scholarbank.nus.edu.sg/handle/10635/174311
ISSN: 2041-1723
DOI: 10.1038/s41467-017-02551-8
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