title: Benzylic C-H trifluoromethylation of phenol derivatives.
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.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, Japan. hamashima@u-shizuoka-ken.ac.jp.
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Egami
authors.forename: Takafumi
authors.initials: T
authors.lastname: Ide
authors.forename: Yuji
authors.initials: Y
authors.lastname: Kawato
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry* / Q000494:pharmacology*; D050753:Enoyl-(Acyl-Carrier-Protein) Reductase (NADH) / Q000037:antagonists & inhibitors* / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008745:Methylation; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D001593:Benzyl Compounds; D004791:Enzyme Inhibitors; D006845:Hydrocarbons, Fluorinated; D010636:Phenols; D050753:Enoyl-(Acyl-Carrier-Protein) Reductase (NADH)