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通过可见光诱导电荷转移实现乙烯基醚的无催化剂分子间磺酰基/氟甲基杂芳基化反应

Catalyst-Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible-Light-Induced Charge Transfer.

作者信息

Long Tianyu, Pan Shiwei, Zhu Shengqing, Chu Lingling

机构信息

State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, Center for Advanced Low-Dimension Materials, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, P. R. China.

出版信息

Chemistry. 2022 Mar 10;28(15):e202104080. doi: 10.1002/chem.202104080. Epub 2022 Feb 23.

Abstract

We report a visible-light-induced three-component sulfonyl-heteroarylation of vinyl ethers with sulfinates and five-membered heteroaryl chlorides. This protocol proceeds via electron-donor-acceptor (EDA) complexes between sulfinates and heteroaryl chlorides, giving β-sulfonyl alkyl five-membered heteroarenes with high efficiency and excellent regioselectivity under mild and catalyst-free conditions. Utilization of CF SO Na or CF HSO Na as coupling partners further achieves three-component fluoromethyl-arylation of vinyl ethers, furnishing a series of valuable CF /CF H-incorporated alkyl heterocycles under mild conditions.

摘要

我们报道了一种可见光诱导的乙烯基醚与亚磺酸盐和五元杂芳基氯化物的三组分磺酰基-杂芳基化反应。该反应通过亚磺酸盐和杂芳基氯化物之间的电子给体-受体(EDA)络合物进行,在温和且无催化剂的条件下高效且具有优异的区域选择性地生成β-磺酰基烷基五元杂芳烃。使用CF₃SO₂Na或CF₃HSO₃Na作为偶联伙伴进一步实现了乙烯基醚的三组分氟甲基-芳基化反应,在温和条件下提供了一系列含有CF₃/CF₃H的烷基杂环化合物。

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