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Copper-mediated 1,2-bis(trifluoromethylation) of arynes†
Chemical Science ( IF 8.4 ) Pub Date : 2018-09-21 00:00:00 , DOI: 10.1039/c8sc03754j
Xinkan Yang 1 , Gavin Chit Tsui 1
Affiliation  

We herein describe an unprecedented 1,2-bis(trifluoromethylation) of arynes with [CuCF3] 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 o-trifluoromethyl aryl radical intermediate via CF3 group transfer from [CuCF3] to the aryne.

中文翻译:

铜介导的芳烃 1,2-双(三氟甲基化)†

我们在此描述了在氧化剂 DDQ 存在下,芳炔与 [CuCF 3 ]发生前所未有的 1,2-双(三氟甲基化) 。该方法允许在温和条件下从芳炔前体一步快速构建一类新的 1,2-双(三氟甲基)芳烃。其合成效用已在双(三氟甲基化)分子的制备中得到证实,具有潜在的制药和材料科学应用。机理研究表明存在邻三氟甲基芳基自由基中间体,通过CF 3基团从[CuCF 3 ]转移到芳炔。
更新日期:2018-09-21
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