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未活化烯烃与喹喔啉-2(1)-酮及相关氮杂环的自由基氟磺酰基杂芳基化反应

Radical Fluorosulfonyl Heteroarylation of Unactivated Alkenes with Quinoxalin-2(1)-ones and Related N-Heterocycles.

作者信息

Lin Lu, Wang Peng, Dong Tao, Tsui Gavin Chit, Liao Saihu

机构信息

Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China.

Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR 12333, China.

出版信息

Org Lett. 2023 Feb 24;25(7):1088-1093. doi: 10.1021/acs.orglett.2c04315. Epub 2023 Feb 12.

Abstract

The incorporation of sulfonyl fluoride groups into molecules has been proved effective to enhance their biological activities or introduce new functions. Herein, we report a transition-metal-free and visible-light-mediated radical 1-fluorosulfonyl-2-heteroarylation of alkenes, which could allow access to a series of SOF-containing quinoxalin-2(1)-ones, which are a critical structural motif widely present in a number of biologically active molecules. Further application of the method to the modification of other heterocycles and drug molecules as well as ligation chemistry via SuFEx click reactions is also demonstrated.

摘要

已证明将磺酰氟基团引入分子中可有效增强其生物活性或引入新功能。在此,我们报道了一种无过渡金属且可见光介导的烯烃自由基1-氟磺酰基-2-杂芳基化反应,该反应可用于合成一系列含SOF的喹喔啉-2(1)-酮,这是一种关键的结构基序,广泛存在于许多生物活性分子中。该方法还被证明可进一步应用于其他杂环和药物分子的修饰以及通过SuFEx点击反应进行连接化学。

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