Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetone / chemistry
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Alkaloids / chemistry
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Antiviral Agents / chemical synthesis
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Antiviral Agents / chemistry
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Chelating Agents / chemistry
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Chlorofluorocarbons, Methane / chemical synthesis*
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Chlorofluorocarbons, Methane / chemistry
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Diacetyl / chemistry
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Green Chemistry Technology / methods
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Hydrocarbons, Aromatic / chemistry*
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Hydrocarbons, Aromatic / radiation effects*
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Indicators and Reagents
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Ketones / chemistry
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Ligands
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Light
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Photochemical Processes
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Ultraviolet Rays
Substances
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Alkaloids
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Antiviral Agents
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Chelating Agents
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Chlorofluorocarbons, Methane
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Hydrocarbons, Aromatic
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Indicators and Reagents
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Ketones
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Ligands
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Acetone
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Diacetyl
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fluoroform