Progress on Fluorination and Fluoroalkylation Reactions of Aryl Sulfonium Salts

doi:10.6023/cjoc202605004

Abstract

Aryl sulfonium salts have exhibited obvious advantages such as simple preparation, structural diversity, good site-selectivity, and rich reactivity, and have emerged as important intermediates for the precise functionalization of arenes. In recent years, aryl sulfonium salts have been widely utilized in fluorination and fluoroalkylation reactions, among which cyclic aryl sulfonium salts such as thianthrenium, phenoxathiinium, dibenzothiophenium, and phenothiazinium salts have attracted particular attention. This article comprehensively summarizes the progress on fluorination and fluoroalkylation reactions of aryl sulfonium salts, which are mainly categorized into three types: 1) Construction of Ar-F and Ar-[¹⁸F] bonds via transition-metal- and visible-light-catalyzed fluorination and aromatic nucleophilic substitution with radioactive [¹⁸F] salts; 2) Formation of Ar-CF₂H, Ar-CF₂COR, Ar-CF₃, and Ar-CF(CF₃)₂ bonds through transition-metal-catalyzed couplings, catalyst-free coupling, and photoinduced radical couplings; 3) Construction of Ar-OCF₃, Ar-SCF₃, Ar-SeCF₃, and Ar-TeCF₃ bonds, involving reaction mechanisms such as transition-metal catalysis, mechanochemical transformation, and photocatalytic activation of electron donor-acceptor (EDA) complexes. These reactions provide important references for the further application of aryl sulfonium salts in fluorine chemistry.

Key words: aryl sulfonium salts, fluorination, [¹⁸F]-labeling, fluoroalkylation

Cite this article

Fu Xiaojing, Wu Ping, Song Jiawei, Xin Xin, Xu Wenjin, Zhang Chengpan. Progress on Fluorination and Fluoroalkylation Reactions of Aryl Sulfonium Salts[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202605004.

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