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Issue 4, 2020
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Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis

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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.

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

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Supplementary files

Article information


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

Chem. Sci., 2020,11, 1026-1031
Article type
Edge Article

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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