硫鎓盐在可见光催化构建C—C键及C—杂原子键中的应用进展

doi:10.6023/cjoc202209004

摘要/Abstract

硫鎓盐是具有三个碳硫键的带正电荷的最重要四价硫化合物之一. 由于硫鎓盐具有较高的化学稳定性、容易制备、结构多样、丰富的反应性等优点, 其作为反应底物在有机合成中得到了广泛应用. 近年来, 可见光促进的有机合成方法学引起了研究者极大的兴趣. 总结了各种硫鎓盐试剂在可见光诱导的自由基型反应中的研究进展, 介绍了各类 C—C键和C—X (X=B, N, O, S, Se, Te, F, Cl, I)键的形成反应, 并对部分反应的适用范围和机理进行了讨论.

关键词: 硫化学, 硫鎓盐, 可见光, 自由基反应

Sulfonium salts are one of the most important class of organosulfur (IV) compounds which have a positive charge on the sulfur center with three C—S bonds. Because of their bench-stable, easy synthesis, broad structural diversity, and rich reactivity, sulfonium salts are playing a significant role in synthetic chemistry. In recent years, visible-light promoted photoredox catalysis is rapidly developing into a powerful tool for organic synthesis. In this paper, the recent advances of different sulfonium salts in the radical type reactions induced by visible light are summarized. The formation reactions of C—C bond and C—X (X=B, N, O, S, Se, Te, F, Cl, I) bonds are introduced, and the applicable scope and mechanism of some reactions are also discussed.

Key words: sulfur chemistry, sulfonium salt, visible light, free radical reaction

引用此文

徐浩, 张杰, 左峻泽, 王丰晓, 吕健, 混旭, 杨道山. 硫鎓盐在可见光催化构建C—C键及C—杂原子键中的应用进展[J]. 有机化学, 2022, 42(12): 4037-4059.

Hao Xu, Jie Zhang, Junze Zuo, Fengxiao Wang, Jian Lü, Xu Hun, Daoshan Yang. Recent Advances in Visible-Light-Catalyzed C—C Bonds and C—Heteroatom Bonds Formation Using Sulfonium Salts[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4037-4059.

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图/表 34

图式1. 硫鎓盐的常规合成方法

Scheme 1. Conventional methods for the synthesis of sulfonium salts

图式2. 硫鎓盐的反应模式

Scheme 2. Reaction mode of sulfonium salts

图式3. 硫鎓盐参与的自由基型反应

Scheme 3. Radical type reactions involving sulfonium salts

图式4. 光诱导硫鎓盐脱硫生成苯乙酮

Scheme 4. Light induced desulphurization of sulfonium salts leading to acetophenone

图式5. 可见光促进的以Umemoto试剂为三氟甲基源的三氟甲基取代菲啶类化合物的合成

Scheme 5. Visible-light-promoted approach to 6-trifluoroethyl phenanthridines using Umemoto’s reagent as the CF3 source

图式6. 光诱导苝催化烯烃的氨化-二氟甲基化反应

Scheme 6. Visible-light-induced perylene-catalyzed aminodifluoromethylation of alkenes

图式7. 可见光诱导羟基烯烃的芳基三氟甲基化反应

Scheme 7. Visible light-induced aryltrifluoromethylation of hydroxy alkenes

图式8. 金属与光协同催化苄基硫鎓盐的自由基烷基化反应

Scheme 8. Metallaphotoredox-catalysed radical alkylation of benzylsulfonium salts

图式9. 光催化硫鎓盐引发的自由基烷基化反应

Scheme 9. Photoredox-catalysed radical alkylation of sulfonium salts

图式10. 可见光促进烷基噻蒽盐与活泼烯烃的脱硫烷基化反应

Scheme 10. Visible-light-promoted desulfurative alkylation of alkyl thianthrenium salts with activated olefins

图式11. 可见光驱动二价铜辅助的三组分反应构建γ-羟基酮类化合物

Scheme 11. Visible-light-driven photoredox-catalyzed and copper(II)-assisted three-component approach to γ-hydroxy carbonyl compounds

图式12. 硫鎓盐作为芳基源的可见光催化还原反应

Scheme 12. Visible-light photocatalytic reduction of sulfonium salts as a source of aryl radicals

图式13. 可见光促进异腈和烯烃的三氟甲基化反应

Scheme 13. Visible-light-promoted trifluoromethylation of isonitrile and olefins

图式14. 苄基硫鎓盐的光催化烯基化反应

Scheme 14. Photoredox-catalyzed alkenylation of benzylsulfoniums

图式15. 烷基硫鎓盐光催化脱硫用于杂芳烃的官能化

Scheme 15. Alkylsulfonium salts for photochemical desulphurizative functionalization of heteroarenes

图式16. 杀虫剂吡丙醚衍生物的间接氰化反应

Scheme 16. Indirect cyanidation of derivatives of insecticide pyrrolyl ether

图式17. 铜光催化芳基硫鎓盐区域选择性交叉偶联构建C(sp2)—C(sp)

Scheme 17. Photoinduced copper-catalyzed site-selective C(sp2)—C(sp) cross-coupling via aryl sulfonium salts

图式18. 光催化合成炔基化吡咯衍生物

Scheme 18. Synthesis of alkynylated pyrrole derivatives by photocatalysis

图式19. 铜催化烷基噻蒽类硫鎓盐的交叉偶联反应

Scheme 19. Copper-catalyzed cross-coupling reactions using alkyl thianthrenium salts

图式20. 铜光催化基于脱硫策略的Sonogashira偶联反应

Scheme 20. Desulphurization strategy for Sonogashira couplings by visible light/copper catalysis

图式21. 无金属光氧化欢迎催化芳烃的C—H/C—H偶联反应

Scheme 21. Metal-free photoredox-catalyzed formal C—H/C—H coupling of arenes

图式22. 硫鎓盐对邻羟基芳基氨基酮的芳基化反应

Scheme 22. Arylation of ortho-Hydroxyarylenaminones by Sulfonium Salts

图式23. 芳基硫鎓盐的光催化芳基化反应

Scheme 23. Photocatalytic arylation of aryl sulfonium salts

图式24. 钯金属光氧化还原催化吲哚衍生物的2-芳基化

Scheme 24. Palladium metallaphotoredox-catalyzed 2?arylation of indole derivatives

图式25. Ritter在芳香族化合物C—H官能化方面的开创性工作

Scheme 25. Ritter’s pioneering work on C—H functionalization of aromatic compounds

图式26. 芳基硫鎓盐的区域选择性C—H氧化反应

Scheme 26. Site-selective C—H oxygenation via aryl sulfonium salts

图式27. Ritter的基于芳基硫鎓盐构筑碳杂原子键的工作

Scheme 27. Ritter’s work on building C-heteroatom bonds using aryl sulfonium salts

图式28. 炔基硫鎓盐用作硫属元素键合催化剂

Scheme 28. Employing alkynyl sulfonium salts as chalcogen-bonding catalysts

图式29. 光诱导碳硫键活化芳基硫鎓盐的硼化反应

Scheme 29. Borylation of aryl sulfonium salts via C—S activation enabled by light

图式30. 以噻蒽类硫鎓盐生成非稳定性烷基自由基构建C—B键

Scheme 30. Generation of non-stabilized alkyl radicals from thianthrenium salts for C—B bond formation

图式31. 可见光引发芳基硫鎓盐与[Me4N][SeCF3]的三氟甲基硒化反应

Scheme 31. Visible-light-initiatede trifluoromethylselenolation of arylsulfonium salts with [Me4N][SeCF3]

图式32. 可见光催化硫鎓盐、二氧化硫和肼的反应

Scheme 32. Visible-light catalyzed reaction of thianthrenium salts, sulfur dioxide and hydrazines

图式33. 光氧化还原催化二氧化硫和噻蒽类硫鎓盐合成酮的α-磺酰化反应

Scheme 33. Photoredox-catalyzed α?sulfonylation of ketones from sulfur dioxide and thianthrenium salts

图式34. 铜光催化硫鎓盐与二硫属化合物的自由基型开环反应

Scheme 34. Radical type ring opening of sulfonium salts with dichalcogenides by visible light and copper catalysis

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