Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 18, Pages 5809-5812Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b02782
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Funding
- Canada Research Chair (Tier 1) foundation
- Natural Sciences and Engineering Research Council of Canada
- Fonds de recherche sur la nature et les technologies
- Canada Foundation for Innovation (CFI)
- McGill University
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We describe a simple, metal- and oxidant free photochemical strategy for the direct trifluoromethylation of unactivated arenes and heteroarenes under either ultraviolet or visible light irradiation. We demonstrated that photoexcited aliphatic ketones, such as acetone and diacetyl, can be used as promising low-cost radical initiators to generate CF3 radicals from sodium triflinate efficiently. The broad utility of this strategy and its benefit to medicinal chemistry are demonstrated by the direct trifluoromethylation of unprotected bidentate chelating ligand, xanthine alkaloids, nucleosides, and related antiviral drug molecules.
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