Photocatalytic Radical Azido/Fluorosulfonylation of Unactivated Alkenes: Accessing Hubs Bridging CuAAC and SuFEx Click Chemistry

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-28 DOI:10.1021/acs.orglett.5c00426

Guanhua Pei, Peng Wang, Lu Lin, Honghai Zhang, Rongbiao Wei, Saihu Liao

引用次数: 0

Abstract

Herein, we describe the successful development of an azido-fluorosulfonylation reaction of alkenes under photoredox catalysis, which could allow the installation of the two “clickable” groups, −N₃ and −SO₂F, on a C–C double bond, with TMSN₃ as the azide source. The utilization of the difunctionalization products is also demonstrated in the construction of a library of 1,2,3-triazolesulfonyl fluoride compounds as well as drug molecule ligation by merging copper-catalyzed azide–alkyne cycloaddition (CuAAC) and sulfur(VI) fluoride exchange (SuFEx), the two generations of click reactions. Mechanistic studies suggest a radical fluorosulfonylation/azidation mechanism and unveil FSO₂N₃ as a new and potential fluorosulfonyl radical precursor.

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非活化烯烃的光催化自由基叠氮/氟磺化：连接CuAAC和SuFEx的枢纽点击化学

本文中，我们描述了在光氧化还原催化下烯烃的叠氮-氟磺酰化反应的成功发展，该反应可以允许在C-C双键上安装两个“可点击”的基团，−N3和−SO2F，以TMSN3为叠氮源。双官能化产物在1,2,3-三唑磺酰氟化合物文库的构建以及铜催化叠氮-炔环加成（CuAAC）和硫（VI）氟交换（SuFEx）两代键合反应的药物分子连接中也得到了应用。机理研究提示了自由基氟磺酰化/叠氮化机制，并揭示了FSO2N3是一种新的潜在的氟磺酰自由基前体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.

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