Trifluoromethyl-containing compounds play a significant role in medicinal chemistry, materials and fine chemistry. Although direct C−H trifluoromethylation has been achieved on Csp2−H bonds, direct conversion of Csp3−H bonds to Csp3−CF3 remains challenging. We report herein an efficient protocol for the selective trifluoromethylation of benzylic C−H bonds. This process is mediated by a combination CuIII−CF3 species and persulfate salts. A wide range of methylarenes can be selectively trifluoromethylated at the benzylic positions. A combination of experimental and theoretical mechanistic studies suggests that the reaction involves a radical intermediate and a CuIII−CF3 species as the CF3 transfer reagent.
All Science Journal Classification (ASJC) codes
- Organic Chemistry