Journal article
Organophotoredox hydrodefluorination of trifluoromethylarenes with translational applicability to drug discovery
- 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.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, 1.7MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.0c03881
Authors
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 142
- Issue:
- 20
- Pages:
- 9181-9187
- Publication date:
- 2020-05-07
- Acceptance date:
- 2020-05-07
- DOI:
- EISSN:
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1520-5126
- ISSN:
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0002-7863
- Language:
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English
- Keywords:
- Subjects:
- Pubs id:
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1105831
- Local pid:
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pubs:1105831
- Deposit date:
-
2020-05-21
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2020
- Rights statement:
- © 2020 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
- Licence:
- CC Attribution (CC BY)
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