Abstract
Phenol derivatives were trifluoromethylated using copper/Togni reagent. In dimethylformamide, the benzylic C-H bond at the para position of the hydroxyl group was selectively substituted with a CF3 group. In contrast, aromatic C-H trifluoromethylation occurred in alcoholic solvents. Practical utility of the reactions was demonstrated by application to the synthesis of a potent enoyl-acyl carrier protein reductase (FabI) inhibitor.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzyl Compounds / chemistry*
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Benzyl Compounds / pharmacology*
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Enoyl-(Acyl-Carrier-Protein) Reductase (NADH) / antagonists & inhibitors*
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Enoyl-(Acyl-Carrier-Protein) Reductase (NADH) / metabolism
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Hydrocarbons, Fluorinated / chemical synthesis
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Hydrocarbons, Fluorinated / chemistry
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Hydrocarbons, Fluorinated / pharmacology*
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Methylation
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Molecular Structure
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Phenols / chemistry*
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Phenols / pharmacology*
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Structure-Activity Relationship
Substances
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Benzyl Compounds
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Enzyme Inhibitors
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Hydrocarbons, Fluorinated
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Phenols
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Enoyl-(Acyl-Carrier-Protein) Reductase (NADH)