Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 45, Pages 11559-11563Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201802766
Keywords
C-H activation; copper; fluorination; late-stage diversification; trifluoromethylation
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Funding
- Miami University
- Ministry of Science and Technology of the Republic of China [MOST 105-2113-M-006-017-MY2]
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Trifluoromethyl-containing compounds play a significant role in medicinal chemistry, materials and fine chemistry. Although direct C-H trifluoromethylation has been achieved on Csp(2)-H bonds, direct conversion of Csp(3)-H bonds to Csp(3)-CF3 remains challenging. We report herein an efficient protocol for the selective tri-fluoromethylation of benzylic C-H bonds. This process is mediated by a combination Cu-III-CF3 species and persulfate salts. A wide range of methylarenes can be selectively tri-fluoromethylated at the benzylic positions. A combination of experimental and theoretical mechanistic studies suggests that the reaction involves a radical intermediate and a Cu-III-CF3 species as the CF3 transfer reagent.
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