Yang Xinkan, Tsui Gavin Chit
Department of Chemistry , The Chinese University of Hong Kong , Shatin , New Territories , Hong Kong SAR . Email:
Chem Sci. 2018 Sep 21;9(47):8871-8875. doi: 10.1039/c8sc03754j. eCollection 2018 Dec 21.
We herein describe an unprecedented 1,2-bis(trifluoromethylation) of arynes with [CuCF] in the presence of an oxidant DDQ. The method allows the rapid construction of a new class of 1,2-bis(trifluoromethyl)arenes in one-step from aryne precursors under mild conditions. Its synthetic utility has been demonstrated in the preparation of bis(trifluoromethylated) molecules with potential pharmaceutical and materials science applications. Mechanistic studies indicated the presence of an -trifluoromethyl aryl radical intermediate CF group transfer from [CuCF] to the aryne.
我们在此描述了在氧化剂DDQ存在下，芳烃与[CuCF]发生前所未有的1,2-双（三氟甲基化）反应。该方法能够在温和条件下，从芳烃前体一步快速构建一类新型的1,2-双（三氟甲基）芳烃。其合成效用已在制备具有潜在药物和材料科学应用的双（三氟甲基化）分子中得到证明。机理研究表明存在一个三氟甲基芳基自由基中间体，即CF基团从[CuCF]转移至芳烃。
