Department of Chemistry, Fuzhou University, Fuzhou 350108 (China), Fax: (+86) 591-22866121.
Chemistry. 2014 Jan 13;20(3):657-61. doi: 10.1002/chem.201303934. Epub 2013 Dec 6.
The development of new strategies for synthesis of trifluoromethylthiolate compounds is of considerable importance in pharmaceuticals, agrochemicals, and advanced materials. Accordingly, currently much attention is being devoted to the development of effective methods and reagents for their synthesis. In contrast, considerably less effort has been afforded to the development of preparing CSeCF3 bonds. Herein we report a concise route to synthesize a family of copper(I) trifluoromethylselenolate reagents by the reaction of CuI with the Ruppert's reagent (Me3 SiCF3 ), KF, and elemental selenium in the presence of dinitrogen ligands in CH3 CN at room temperature. The reagent [Cu(bpy)(SeCF3 )]2 was proven to be air-stable and highly efficient for nucleophilic trifluoromethylthselenolation of a broad range of (hetero)aryl halides and alkyl halides. This method represents a powerful protocol for the construction trifluoromethylselenolate compounds.
新型三氟甲基硫代化合物合成策略的发展在制药、农化和先进材料领域具有重要意义。因此，目前人们非常关注开发有效的方法和试剂来合成它们。相比之下，人们在开发制备 CSeCF3 键方面的努力要少得多。在此，我们报告了一种简洁的方法，即在氮气配体存在下，在 CH3 CN 中，室温下用 CuI 与 Ruppert 试剂（Me3 SiCF3 ）、KF 和元素硒反应，合成了一系列铜（I）三氟甲基硒代物试剂。证明试剂 [Cu(bpy)(SeCF3 )]2 对各种（杂）芳基卤化物和烷基卤化物的亲核三氟甲基硒代反应具有空气稳定性和高效性。该方法代表了构建三氟甲基硒代化合物的有力方案。
