芳基锍盐的氟化和氟烷基化反应研究进展

doi:10.6023/cjoc202605004

摘要/Abstract

芳基锍盐因制备简单、结构多样、位点选择性好和反应性质丰富等优点, 已成为芳烃精准官能团化的重要原料. 近年来, 芳基锍盐在氟化及氟烷基化反应中得到了广泛应用, 其中环状芳基锍盐如噻蒽锍盐、吩噁噻锍盐、二苯并噻吩锍盐和吩噻嗪锍盐等尤为受到关注. 此文全面总结了芳基锍盐参与的氟化和氟烷基化反应, 主要分为以下三类: (1) Ar—F键与Ar—[¹⁸F]键的构建, 包括过渡金属和可见光协同催化的氟化反应, 以及放射性[¹⁸F]标记的芳香亲核取代反应; (2) Ar—CF₂H键、Ar—CF₂COR键、Ar—CF₃键和Ar—CF(CF₃)₂键的构建, 涵盖过渡金属催化的偶联、无催化剂参与的偶联以及光诱导的自由基偶联等; (3) Ar—OCF₃键、Ar—SCF₃键、Ar—SeCF₃键及Ar—TeCF₃键的构建, 涉及的反应机理包括过渡金属催化、机械化学转化以及光催化电子供体-受体(EDA)复合物活化等. 这些反应为芳基锍盐在氟化学中的进一步应用提供了重要参考.

关键词: 芳基锍盐, 氟化, [¹⁸F]标记, 氟烷基化

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 in 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 couplings, 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 transformations, and photocatalytic activation of electron donor-acceptor (EDA) complexes. These reactions provide important references for the further applications of aryl sulfonium salts in fluorine chemistry.

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

引用此文

浮晓静, 吴萍, 宋佳威, 辛鑫, 徐文瑨, 张成潘. 芳基锍盐的氟化和氟烷基化反应研究进展[J]. 有机化学, 2026, 46(9): 3431-3447.

Xiaojing Fu, Ping Wu, Jiawei Song, Xin Xin, Wenjin Xu, Chengpan Zhang. Progress on Fluorination and Fluoroalkylation Reactions of Aryl Sulfonium Salts[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3431-3447.

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图/表 21

图1. 蓝光和铱/铜协同催化CsF对芳基噻蒽锍盐的氟化反应

Figure 1. Blue-light-driven and Ir/Cu dual-catalyzed fluorination of aryl thianthrenium salts with CsF

图2. 三芳基锍盐的亲核[18F]氟化反应

Figure 2. Nucleophilic [18F]fluorination of triarylsulfonium salts

图3. 三芳基锍盐介导复杂芳烃的[18F]标记

Figure 3. [18F]-Labeling of complex small molecules via triarylsulfonium salt intermediates

图4. 由联芳基硫醚环化构建的芳基二苯并噻吩锍盐的[18F]标记

Figure 4. [18F]-Labeling of aryl dibenzothiophenium salts derived from cyclization of aryl biaryl sulfides

图5. 芳基二苯并噻吩锍盐的亲核[18F]氟化反应

Figure 5. Nucleophilic [18F]fluorination of aryl dibenzothiophenium salts

图6. 钯催化(DMPU)2Zn(CF2H)2对芳基噻蒽锍盐的二氟甲基化和二氟乙酰化反应

Figure 6. Palladium-catalyzed difluoromethylation and difluoroacetylation of aryl thianthrenium salts with (DMPU)2Zn(CF2H)2

图7. 铜催化(DMPU)2Zn(CF2H)2对烯基噻蒽锍盐的二氟甲基化反应

Figure 7. Copper-catalyzed difluoromethylation of alkenyl thianthrenium salts with (DMPU)2Zn(CF2H)2

图8. 钯催化ClCF2CO2Et对芳基噻蒽锍盐的二氟甲基化反应

Figure 8. Palladium-catalyzed difluoromethylation of aryl thianthrenium salts with ClCF2CO2Et

图9. 无催化剂参与下TMSCF2H对芳基吩噻嗪锍盐和芳基吩噁噻锍盐的二氟甲基化反应

Figure 9. Catalyst-free difluoromethylation of aryl phenothiazinium/phenoxathiinium salts with TMSCF2H

图10. 绿光和铱/铜协同催化YCF2COR对芳基锍盐的二氟烷基化反应

Figure 10. Green-light-induced and Ir/Cu-cocatalyzed difluoroalkylation of aryl sulfonium salts with YCF2COR

图11. 蓝光和钌协同催化原位生成的CuCF3对芳基噻蒽锍盐的三氟甲基化反应

Figure 11. Blue-light- and Ru-catalyzed trifluoromethylation of aryl thianthrenium salts with the in situ formed CuCF3

图12. BINAP加速蓝光/铜协同催化CuCF3对芳基噻蒽锍盐的三氟甲基化反应

Figure 12. BINAP-accelerated blue-light- and copper-catalyzed trifluoromethylation of aryl thianthrenium salts with CuCF3

图13. 蓝光和铜催化(DMPU)2Zn(Rfn)2对芳基噻蒽锍盐的全氟烷基化反应

Figure 13. Blue-light- and copper-catalyzed perfluoroalkylation of aryl thianthrenium salts with (DMPU)2Zn(Rfn)2

图14. 光诱导铜催化Yagupolskii-Umemoto试剂对芳基噻蒽锍盐的三氟甲基化反应

Figure 14. Photoinduced copper-mediated trifluoromethylation of aryl thianthrenium salts with Yagupolskii-Umemoto reagent

图15. 蓝光和钌/铜协同催化CF2[18F]I对芳基噻蒽锍盐的[18F]三氟甲基化反应

Figure 15. Blue-light- and Ru/Cu-cocatalyzed [18F]trifluoromethylation of aryl thianthrenium salts with CF2[18F]I

图16. 可见光和铱/铜协同催化AgCF(CF3)2对芳基噻蒽锍盐的七氟异丙基化反应

Figure 16. Visible-light- and Ir/Cu-cocatalyzed heptafluoroisopropylation of aryl thianthrenium salts with AgCF(CF3)2

图17. 机械球磨和钴介导芳基二甲基锍盐的三氟甲氧基化反应

Figure 17. Mechanochemical and cobalt-mediated trifluoromethoxylation of aryl dimethylsulfonium salts

图18. 可见光和钌/铜协同催化[Me4N][SCF3]对芳基四氟噻蒽锍盐的三氟甲硫基化反应

Figure 18. Visible-light- and Ru/Cu-cocatalyzed trifluoromethylthiolation of aryl tetrafluorothianthrenium salts with [Me4N][SCF3]

图19. 钌催化[Me4N][SCF3]对烯基噻蒽锍盐的三氟甲硫基化反应

Figure 19. Ruthenium-catalyzed trifluoromethylthiolation of alkenyl thianthrenium salts with [Me4N][SCF3]

图20. 蓝光诱导[Me4N][SeCF3]对芳基二苯并噻吩锍盐的三氟甲硒基化反应

Figure 20. Blue-light-induced trifluoromethylselenolation of aryl dibenzothiophenium salts with [Me4N][SeCF3]

图21. 无催化剂参与下绿光诱导[Me4N][TeCF3]对芳基锍盐的三氟甲碲基化反应

Figure 21. Green-light-induced catalyst-free trifluoromethyltelluration of aryl sulfonium salts with [Me4N][TeCF3]

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