Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 20, Pages 9181-9187Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c03881
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Funding
- Engineering and Physical Sciences Research Council [EP/N509711/1]
- European Union's Horizon 2020 research and innovation program under Marie Sklodowska-Curie Grant [721902, 840724]
- Marie Curie Actions (MSCA) [840724] Funding Source: Marie Curie Actions (MSCA)
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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.
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