Semiconductor photocatalysis to engineering deuterated N-alkyl pharmaceuticals enabled by synergistic activation of water and alkanols

Zhaofei Zhang, Chuntian Qiu, Yangsen Xu, Qing Han, Junwang Tang, Kian Ping Loh and Chenliang Su ()
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Zhaofei Zhang: Shenzhen University
Chuntian Qiu: Shenzhen University
Yangsen Xu: Shenzhen University
Qing Han: University College London
Junwang Tang: University College London
Kian Ping Loh: National University of Singapore
Chenliang Su: Shenzhen University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Precisely controlled deuterium labeling at specific sites of N-alkyl drugs is crucial in drug-development as over 50% of the top-selling drugs contain N-alkyl groups, in which it is very challenging to selectively replace protons with deuterium atoms. With the goal of achieving controllable isotope-labeling in N-alkylated amines, we herein rationally design photocatalytic water-splitting to furnish [H] or [D] and isotope alkanol-oxidation by photoexcited electron-hole pairs on a polymeric semiconductor. The controlled installation of N-CH3, -CDH2, -CD2H, -CD3, and -13CH3 groups into pharmaceutical amines thus has been demonstrated by tuning isotopic water and methanol. More than 50 examples with a wide range of functionalities are presented, demonstrating the universal applicability and mildness of this strategy. Gram-scale production has been realized, paving the way for the practical photosynthesis of pharmaceuticals.

Date: 2020
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DOI: 10.1038/s41467-020-18458-w

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