铜催化的盐酸芳肼、DABSO 和 NFSI 的三组分反应合成芳磺酰氟。
Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides.
机构信息
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, China.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
出版信息
Org Biomol Chem. 2021 Oct 27;19(41):8999-9003. doi: 10.1039/d1ob01697k.
This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source and -fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.
本文报道了一种在温和条件下，利用 1,4-二氮杂二环[2.2.2]辛烷双(二氧杂环戊烷)(DABSO)作为磺酰源和-氟苯磺酰亚胺(NFSI)作为氟源，在铜催化下，芳基腙盐酸盐经三步转化为芳基磺酰氟的简便方法，产率较高。该反应基于自由基二氧化硫插入和氟化策略。值得注意的是，芳基腙盐酸盐可用作芳基自由基的安全前体。
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