铜促进四氟硼酸重氮苯与三氟甲亚磺酸钠的三氟甲磺酰化和三氟甲基化反应
Copper-Promoted Trifluoromethanesulfonylation and Trifluoromethylation of Arenediazonium Tetrafluoroborates with NaSO2CF3.
作者信息
Zhang Ke, Xu Xiu-Hua, Qing Feng-Ling
机构信息
†College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China.
‡Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
出版信息
J Org Chem. 2015 Aug 7;80(15):7658-65. doi: 10.1021/acs.joc.5b01295. Epub 2015 Jul 24.
A tunable chemoselective trifluoromethanesulfonylation and trifluoromethylation of arenediazonium tetrafluoroborates with Langlois' reagent (NaSO2CF3) was developed. The Cu2O-catalyzed reaction in DMSO gave aryl trifluoromethanesulfones as the major products. On the other hand, the trifluoromethylated arenes were produced in the presence of oxidant tert-butyl hydroperoxide, CuBF4(MeCN)4, and 2,2';6',2″-terpyridine (tpy). Both of these transformations proceed under mild conditions and tolerate functional groups.
开发了一种使用朗格卢瓦试剂（NaSO2CF3）对四氟硼酸重氮盐进行可调谐的化学选择性三氟甲磺酰化和三氟甲基化反应。在二甲基亚砜中由氧化亚铜催化的反应以芳基三氟甲砜为主要产物。另一方面，在氧化剂叔丁基过氧化氢、CuBF4(MeCN)4和2,2';6',2″-三联吡啶（tpy）存在的情况下生成三氟甲基化芳烃。这两种转化反应均在温和条件下进行，并且对官能团具有耐受性。
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