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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.

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Publication details

The article was received on 11 Oct 2019, accepted on 04 Dec 2019 and first published on 04 Dec 2019


Article type: Edge Article
DOI: 10.1039/C9SC05132E
Chem. Sci., 2020, Accepted Manuscript
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Formyl-Selective Deuteration of Aldehydes with D2O via Synergistic Organic and Photoredox Catalysis

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

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