Department of Chemistry and Biochemistry, Miami University, 651. E. High Street, Oxford, Ohio, 45056, USA.
Department of Chemistry, National Cheng Kung University, 1 University Road, Tainan City, Taiwan.
Chemistry. 2018 Aug 9;24(45):11559-11563. doi: 10.1002/chem.201802766. Epub 2018 Jul 18.
Trifluoromethyl-containing compounds play a significant role in medicinal chemistry, materials and fine chemistry. Although direct C-H trifluoromethylation has been achieved on Csp -H bonds, direct conversion of Csp -H bonds to Csp -CF remains challenging. We report herein an efficient protocol for the selective trifluoromethylation of benzylic C-H bonds. This process is mediated by a combination Cu -CF 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 Cu -CF species as the CF transfer reagent.
含三氟甲基的化合物在药物化学、材料化学和精细化学中起着重要的作用。尽管已经在 Csp -H 键上实现了直接的 C-H 三氟甲基化，但 Csp -H 键到 Csp -CF 的直接转化仍然具有挑战性。我们在此报告了一种有效且选择性的苄位 C-H 键三氟甲基化方法。该过程是由 Cu-CF 物种和过硫酸盐盐共同介导的。多种甲基芳烃可以在苄位上被选择性地三氟甲基化。实验和理论的综合研究表明，该反应涉及自由基中间体和 Cu-CF 物种作为 CF 转移试剂。
