Organophotoredox Hydrodefluorination of Trifluoromethylarenes with Translational Applicability to Drug Discovery

Jeroen B.I. Sap, Natan J.W. Straathof, Thomas Knauber, Claudio F. Meyer, Maurice Médebielle, Laura Buglioni, Christophe Genicot, Andrés A. Trabanco, Timothy Noël, Christopher W. Am Ende, Véronique Gouverneur (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

13 Citations (Scopus)

Abstract

Molecular editing such as insertion, deletion, and single atom exchange in highly functionalized compounds is an aspirational goal for all chemists. Here, we disclose a photoredox protocol for the replacement of a single fluorine atom with hydrogen in electron-deficient trifluoromethylarenes including complex drug molecules. A robustness screening experiment shows that this reductive defluorination tolerates a range of functional groups and heterocycles commonly found in bioactive molecules. Preliminary studies allude to a catalytic cycle whereby the excited state of the organophotocatalyst is reductively quenched by the hydrogen atom donor, and returned in its original oxidation state by the trifluoromethylarene.

Original languageEnglish
Pages (from-to)9181-9187
Number of pages7
JournalJournal of the American Chemical Society
Volume142
Issue number20
DOIs
Publication statusPublished - 20 May 2020

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