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芳基磺酰氟的合成:钯催化芳基噻蒽鎓盐的氟磺酰化反应。

Aryl sulfonyl fluoride synthesis palladium-catalyzed fluorosulfonylation of aryl thianthrenium salts.

作者信息

Shan Lingling, Ma Zhanhu, Ou Caiyun, Cai Yinxia, Ma Yuyang, Guo Yong, Ma Xiaoyu, Liu Chao

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. 2023 May 10;21(18):3789-3793. doi: 10.1039/d3ob00462g.

Abstract

We developed an efficient palladium-catalyzed fluorosulfonylation reaction of aryl thianthrenium salts to smoothly prepare various aryl sulfonyl fluorides using cheap NaSO as a convenient sulfonyl source in combination with -fluorobenzenesulfonimide (NFSI) as an ideal fluorine source under mild reduction conditions. A one-pot synthesis of aryl sulfonyl fluorides starting from various arenes was established as well without the need for separating aryl thianthrenium salts. The practicality of this protocol was demonstrated by gram-scale synthesis, derivatization reactions, and excellent yields.

摘要

我们开发了一种高效的钯催化芳基噻蒽鎓盐的氟磺酰化反应,以廉价的NaSO作为方便的磺酰基源,与-氟苯磺酰亚胺(NFSI)作为理想的氟源,在温和的还原条件下顺利制备各种芳基磺酰氟。还建立了一种从各种芳烃开始的一锅法合成芳基磺酰氟的方法,无需分离芳基噻蒽鎓盐。通过克级合成、衍生化反应和优异的产率证明了该方法的实用性。

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