Organophotocatalytic α-deuteration of unprotected primary amines via H/D exchange with D2O

Xiang Meng; Yue Dong; Qiangqiang Liu; Wei Wang

doi:10.1039/D3CC04634F

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Organophotocatalytic α-deuteration of unprotected primary amines via H/D exchange with D₂O†

Xiang Meng,^a Yue Dong,^a Qiangqiang Liu^a and Wei Wang

*^abc

Author affiliations

* Corresponding authors

^a Department of Pharmacology and Toxicology, R. Ken Coit College of Pharmacy, University of Arizona, USA
E-mail: weiwang1@arizona.edu

^b Department of Chemistry and Biochemistry, University of Arizona, USA

^c University of Arizona Cancer Centre, University of Arizona, 1703 E. Mabel Street, Tucson, AZ 85721-0207, USA

Abstract

We report a straightforward H/D exchange method for the synthesis of α-deuterated primary amines from a diverse set of primary amines with high levels of deuteration and chemo- and site selectivity and preparative utility. This cost-effective strategy enables the direct conversion of primary amines to α-deuterated counterparts using D₂O as the deuterium source under mild reaction conditions without requiring additional functionality manipulation and with minimal byproduct production.

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Article information

DOI: https://doi.org/10.1039/D3CC04634F
Article type: Communication
Submitted: 22 Sep 2023
Accepted: 28 Nov 2023
First published: 28 Nov 2023

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Chem. Commun., 2024,60, 296-299

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Organophotocatalytic α-deuteration of unprotected primary amines via H/D exchange with D₂O

X. Meng, Y. Dong, Q. Liu and W. Wang, Chem. Commun., 2024, 60, 296 DOI: 10.1039/D3CC04634F

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