硫/硒代磺酸酯作为自由基试剂的应用研究

doi:10.6023/cjoc202204037

摘要/Abstract

硫/硒代磺酸酯是天然产物、合成的生物活性分子和上市药物中的关键结构骨架, 同时也是有机合成中重要的构建原料, 被广泛应用于药物分子和材料科学. 随着过渡金属催化、光催化以及电催化自由基反应的迅速发展, 自由基化学在合成领域取得了突破性进展, 硫/硒代磺酸酯作为自由基试剂的应用也受到了广泛的关注. 分别阐述了近年来快速发展的金属催化、可见光催化、金属和光协同催化以及其它类型催化中硫/硒代磺酸酯作为自由基试剂的应用研究, 并对部分反应的机理进行了详细论述.

关键词: 硫/硒代磺酸酯, 自由基, 催化

Thios/selenium sulfonates are key structural skeletons in natural products, synthetic bioactive molecules and marketed therapeutic drugs, as well as important building material in organic synthesis, and are widely used in drug molecules and materials science. With the rapid development of transition metal-catalyzed, photocatalytic and electrocatalytic radical reactions, breakthroughs in radical chemistry have been achieved in the field of synthesis. Therefore, the applications of thios/selenium sulfonates as radical reagent have attracted extensive attention. The applications of thios/selenium sulfonates as radical reagent in metal catalysis, visible light catalysis, metal-light synergistic catalysis and other types of catalysis, which have been developed rapidly in recent years, are reviewed, and the mechanisms of some reactions are discussed in detail.

Key words: thios/selenium sulfonate, radical, catalysis

引用此文

于婷婷, 宋冬雪, 许颖, 刘冰, 陈宁, 刘颖杰. 硫/硒代磺酸酯作为自由基试剂的应用研究[J]. 有机化学, 2022, 42(12): 4202-4219.

Tingting Yu, Dongxue Song, Ying Xu, Bing Liu, Ning Chen, Yingjie Liu. Study on the Application of Thios/Selenium Sulfonates as Radical Reagent[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4202-4219.

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图/表 46

图1. 含硫/硒的天然产物、药物和生物活性分子

Figure 1. Examples of S/Se-containing natural products, pharmaceuticals and bioactive molecules

图式1. Ag催化的二氟甲基硫代化反应

Scheme 1. Silver catalyzed difluoromethylthiolation

图式2. Cu催化烯烃和胺的磺酰化反应

Scheme 2. Copper catalyzed sulfonylation of alkenes and amines

图式3. Cu催化烯烃氧化三功能化反应

Scheme 3. Copper catalyzed oxidative trifunctionalization of olefins

图式4. Cu催化苯乙烯的双功能化反应

Scheme 4. Copper catalyzed bifunctionalization of styrenes

图式5. Cu催化苯乙烯双功能化反应可能的机制

Scheme 5. Possible mechanism of copper catalyzed bifunctionalization of styrenes

图式6. 光诱导烯烃的硫代磺酰化反应

Scheme 6. Light-induced thiosulfonylation of alkenes

图式7. 光诱导合成硫代二苯并呋喃衍生物

Scheme 7. Light-induced synthesis of thio-substituted dibenzofuran derivatives

图式8. 光诱导1-烯丙基-2-乙炔基苯并咪唑的自由基串联反应

Scheme 8. Light-induced radical cascade reaction of 1-allyl-2-ethynylbenzoimidazoles

图式9. 光诱导1-烯丙基-2-乙炔基苯并咪唑可能的反应途径

Scheme 9. Possible pathways for light-induced 1-allyl-2-ethynylbenzoimidazoles

图式10. 光诱导丁烯基苯并噻唑砜衍生物的1,2,4三功能化

Scheme 10. Light-induced 1,2,4-trifunctionalization of butenyl benzothiazole sulfone derivatives

图式11. 丁烯基苯并噻唑砜衍生物的1,2,4三功能化反应机理

Scheme 11. Mechanism of 1,2,4-trifunctionalization of butenyl benzothiazole sulfone derivatives

图式12. 光诱导乙烯基环丙烷的1,5-三氟甲基硫代磺酰化反应

Scheme 12. Light-induced 1,5-trifluomethylthio-sulfonylation of vinylcyclopropane

图式13. 光诱导的1,5-三氟甲基硫代磺酰化可能的反应机理

Scheme 13. Possible mechanism of light-induced 1,5-trifluo- methylthio-sulfonylation

图式14. 光诱导C—S/Se键的构筑

Scheme 14. Construction of photoinduced C—S/Se bond

图式15. 光诱导二氢吡啶的交叉偶联反应

Scheme 15. Light-induced cross-coupling reaction of dihydropyridines

图式16. 可见光催化芳基重氮盐氘代硫/硒甲基化反应

Scheme 16. Visible light-catalyzed deuterated thiomethylation/ methylselenation of aryldiazonium salts

图式17. 芳基重氮盐氘代硫/硒甲基化反应机理

Scheme 17. Mechanism of deuterated thiomethylation/methylselenation of aryldiazonium salts

图式18. 光诱导硫代氨基甲酸酯的合成

Scheme 18. Light-induced synthesis of thiocarbamates

图式19. 光诱导不对称烷基-烷基硒/硫化物的构建

Scheme 19. Construction of light-induced unsymmetrical alkyl-alkyl selenides/sulfides

图式20. 不对称烷基-烷基硒/硫化物构建的反应机理

Scheme 20. Mechanism of constructing unsymmetrical alkyl-alkyl selenides/sulfides

图式21. 光诱导亚硒酸酯对乙烯基重氮化合物的1,3-自由基加成

Scheme 21. Light-induced radical 1,3-addition of selenosulfonates to vinyldiazo compounds

图式22. 1,3-硒代磺酰化可能的反应途径

Scheme 22. Possible pathways for 1,3-selenosulfonylation

图式23. 光诱导炔系环己二酮的环化

Scheme 23. Visible-light induced cyclization of alkyne-tethered cyclohexadienones

图式24. 金和光氧化还原催化烯烃的硫代磺酰化

Scheme 24. Gold and photoredox catalyzed thiosulfonylation of alkenes

图式25. 铜/光氧化还原协同催化苯乙烯和硫代磺酸酯的ATRA反应

Scheme 25. Copper/photoredox catalyzed ATRA of styrenes and thiosulfonates

图式26. 铜/光氧化还原协同催化苯乙烯和硫代磺酸酯的ATRA反应机理

Scheme 26. Mechanism of copper/photoredox catalyzed ATRA of styrenes and thiosulfonates

图式27. 金/光氧化还原共催化炔烃的原子转移硫代磺酰化

Scheme 27. Gold/photoredox-cocatalyzed atom transfer thiosulfonylation of alkynes

图式28. 炔烃的原子转移硫代磺酰化反应机理

Scheme 28. Mechanism of atom transfer thiosulfonylation of alkynes

图式29. 可见光诱导Co或Cu催化炔烃的硒磺酰化

Scheme 29. Visible light-induced Co or Cu-catalyzed selenosulfonylation of alkynes

图式30. β-(苯硒基)乙烯基砜的制备

Scheme 30. Preparation of β-(phenylseleno)vinyl sulfones

图式31. 烯烃的脱硫硫代烷基化反应

Scheme 31. Desulfitative thioalkylation of alkenes

图式32. 含氧1,7-烯炔的无金属自由基环化反应

Scheme 32. Metal-free radical annulation of oxygen-containing 1,7-enynes

图式33. 碘催化仲硫代氨基甲酸酯的合成

Scheme 33. Iodide-catalyzed synthesis of secondary thiocarbamates

图式34. 合成硫代氨基甲酸酯可能的反应机理

Scheme 34. Possible mechanism for the synthesis of thiocarbamates

图式35. 碘介导硫代磺酸酯与苯乙烯衍生物的偶联反应

Scheme 35. I2-mediated coupling reactions of thiosulfonates and styrene derivatives

图式36. 乙烯基砜的合成机理

Scheme 36. Mechanism of the synthesis of vinyl sulfone

图式37. 区域选择性合成多种羟基砜

Scheme 37. Regioselective synthesis of diverse β-hydroxysulfones

图式38. 硫代磺酸酯与烯烃和硫代磺酸酯与2-苯基-环氧乙烷的反应机理

Scheme 38. Mechanism of thiosulfonates with alkenes and thiosulfonates with styrene oxide

图式39. Cs2CO3介导烯烃的自由基磺酰化反应

Scheme 39. Cs2CO3-mediated radical sulfonylation of alkenes

图式40. 不对称二硫化物的制备

Scheme 40. Preparation of unsymmetrical disulfides

图式41. 异氰化物与硒磺酸酯的自由基链式反应

Scheme 41. Radical-chain reaction of isocyanides with selenosulfonates

图式42. 异氰化物与硒磺酸酯的自由基链式反应机制

Scheme 42. Radical-chain reaction mechanism of isocyanides with selenosulfonates

图式43. 无金属条件下N-(碳硒酸酯)苯并咪唑酮的构建

Scheme 43. Construction of N-(carboselenoate) benzimidazolones under metal-free condition

图式44. 无金属条件下N-(碳硒酸酯)苯并咪唑酮的合成机理

Scheme 44. Synthesis mechanism of N-(carboselenoate) benzimidazolones under metal-free condition

图式45. 硫代磺酸酯的化学选择性插入反应

Scheme 45. Chemoselective insertion reaction of thiosulfonates

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