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通过铜催化的迈尔温芳基化反应合成α-溴芳基乙基磺酰氟和β-芳基乙烯基磺酰氟

Synthesis of α-Bromo Arylethyl Sulfonyl Fluorides and β-Arylethenesulfonyl Fluorides via Copper-Catalyzed Meerwein Arylation.

作者信息

Liu Ming-Jian, Fayad Eman, Abu Ali Ola A, Tao Xiang-Feng, Qin Hua-Li

机构信息

State Key Laboratory of Silicate Materials for Architectures and School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, People's Republic of China.

Department of Biotechnology, College of Sciences, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia.

出版信息

J Org Chem. 2024 Sep 20;89(18):13709-13718. doi: 10.1021/acs.joc.4c01002. Epub 2024 Aug 16.

DOI:10.1021/acs.joc.4c01002
PMID:39151070
Abstract

A practical copper-catalyzed process for the synthesis of the β-arylethenesulfonyl fluorides is described. A series of α-bromo arylethyl sulfonyl fluorides was prepared via Meerwein reaction from arenediazonium tetrafluoroborates and ethenesulfonyl fluoride (ESF) under mild conditions. The following β-arylethenesulfonyl fluorides were further obtained through a β-elimination reaction. This protocol features excellent regio- and stereoselectivity and broad substrate scope.

摘要

描述了一种实用的铜催化合成β-芳基乙烯基磺酰氟的方法。在温和条件下,通过 Meerwein 反应由四氟硼酸重氮盐和乙烯基磺酰氟(ESF)制备了一系列α-溴芳基乙基磺酰氟。通过β-消除反应进一步得到了以下β-芳基乙烯基磺酰氟。该方法具有优异的区域和立体选择性以及广泛的底物范围。

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