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- Title
Copper‐Mediated Trifluoromethylation of Benzylic Csp<sup>3</sup>−H Bonds.
- Authors
Paeth, Matthew; Carson, William; Luo, Jheng‐Hua; Tierney, David; Cao, Zhi; Cheng, Mu‐Jeng; Liu, Wei
- Abstract
Abstract: 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.
- Subjects
COPPER compounds; METHYLATION; BENZYLIC group; HYDROGEN bonding; PHARMACEUTICAL chemistry; PERSULFATES
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 45, p11559
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.201802766