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锰催化实现的重氮化合物的可见光诱导三氟甲基磺酰化反应

Visible-Light-Induced Trifluoromethylsulfonylation Reaction of Diazo Compounds Enabled by Manganese Catalysis.

作者信息

Bai Jinrui, Li Shijia, Qi Dan, Song Zhuoheng, Li Bin, Guo Lin, Song Lijuan, Xia Wujiong

机构信息

State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology (Shenzhen), Shenzhen 518055, China.

Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology (HKUST), Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.

出版信息

Org Lett. 2023 Apr 14;25(14):2410-2414. doi: 10.1021/acs.orglett.3c00490. Epub 2023 Mar 30.

Abstract

A visible-light-induced trifluoromethylsulfonylation reaction of diazo compounds is herein reported. This developed synthetic method captures the relatively rare trifluoromethyl sulfone radicals via coordination to the Mn(acac) catalyst, delivering the corresponding α-trifluoromethyl sulfone esters in good to moderate yields (up to 82%). This protocol exhibits broad substrate scope and is easily carried out under mild reaction conditions. Furthermore, a plausible mechanism of the reaction was investigated through DFT calculations.

摘要

本文报道了一种可见光诱导的重氮化合物三氟甲基磺酰化反应。这种新开发的合成方法通过与Mn(acac)催化剂配位捕获相对罕见的三氟甲基砜自由基,以良好至中等的产率(高达82%)得到相应的α-三氟甲基砜酯。该方法具有广泛的底物范围,并且在温和的反应条件下易于进行。此外,通过密度泛函理论(DFT)计算研究了该反应可能的机理。

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