Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis

Jianyang Dong; Xiaochen Wang; Zhen Wang; Hongjian Song; Yuxiu Liu; Qingmin Wang

doi:10.1039/C9SC05132E

Formyl-selective deuteration of aldehydes with D₂O via synergistic organic and photoredox catalysis†

Jianyang Dong,^a Xiaochen Wang,^a Zhen Wang,^a Hongjian Song,^a Yuxiu Liu

^a and Qingmin Wang

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China
E-mail: wangqm@nankai.edu.cn

Abstract

Formyl-selective deuteration of aldehydes is of high interest for labeling purposes and for optimizing properties of drug candidates. Herein, we report a mild general method for formyl-selective deuterium labeling of aldehydes with D₂O, an inexpensive deuterium source, via a synergistic combination of light-driven, polyoxometalate-facilitated hydrogen atom transfer and thiol catalysis. This highly efficient, scalable reaction showed excellent deuterium incorporation, a broad substrate scope, and excellent functional group tolerance and selectivity and is therefore a practical method for late-stage modification of synthetic intermediates in medicinal chemistry and for generating libraries of deuterated compounds.

This article is part of the themed collections: Celebrating 100 Years of Chemistry at Nankai University, Most popular 2019-2020 organic chemistry articles and In celebration of Chinese New Year

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Article information

DOI: https://doi.org/10.1039/C9SC05132E
Article type: Edge Article
Submitted: 11 Oct 2019
Accepted: 04 Dec 2019
First published: 04 Dec 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2020,11, 1026-1031

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Formyl-selective deuteration of aldehydes with D₂O via synergistic organic and photoredox catalysis

J. Dong, X. Wang, Z. Wang, H. Song, Y. Liu and Q. Wang, Chem. Sci., 2020, 11, 1026 DOI: 10.1039/C9SC05132E

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