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

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.

SUBMITTER: Dong J

PROVIDER: S-EPMC8145436 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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

Dong Jianyang J Wang Xiaochen X Wang Zhen Z Song Hongjian H Liu Yuxiu Y Wang Qingmin Q

Chemical science 20191204 4

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 su ...[more]

PMID: 34084358

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