可见光氧化还原催化炔基化反应的研究进展

doi:10.6023/cjoc202303020

摘要/Abstract

炔烃的合成与转化一直是合成化学领域一个重要的研究内容, 如何在有机分子中高效快速地引入炔基官能团一直备受关注. 光氧化还原催化可利用绿色清洁的光能在较为温和的条件下产生高活性的自由基中间体, 被广泛地应用于有机合成中. 相对于传统过渡金属催化的Sonogashira反应, 光氧化还原催化炔基化反应在最近十年取得了长足发展, 且与前者形成了很好的互补之势. 该类炔基化反应既可通过端炔与铜形成的炔铜中间体进行, 又可通过非端炔的炔基自由基或炔基的自由基加成消除进行. 此外, 由于能用于该光催化炔基化反应的自由基源种类众多, 使得传统Sonogashira反应类型得到了很好补充. 根据炔基化反应成键的类型, 对近年来可见光促进的炔基化反应进行了简要总结.

关键词: 炔基化, 自由基, 光氧化还原, Sonogashira偶联

The synthesis and transformations of alkynes have held an important position in the field of organic synthesis. How to rapidly introduce alkynyl into organic molecules has been of great interest. Photoredox catalysis has been widely used in organic synthesis because it can generate high reactive free radical intermediates under mild conditions using green and clean energy. Visible light photocatalytic alkynylation has flourished in the last decade, which is believed to be a significant complement to the classic transition-metal-catalyzed Sonogashira reaction. This alkynylation could take place via in situ generated copper acetylide complex from terminal alkynes and copper, which also occurs through alkynyl radical species or radical addition elimination of non-terminal alkynes. Moreover, it was a good supplement to Sonogashira reaction that various radical precursors could be applied to alkynylation by visible-light photoredox catalysis. Based on the type of bonding of alkynylation, the research progress of alkynylation reactions by visible-light photoredox catalysis is reviewed, and the future development of this field is prospected.

Key words: alkynylation, radicals, photoredox, Sonogashira coupling

引用此文

归春明, 周潼瑶, 王海峰, 严琼姣, 汪伟, 黄锦, 陈芬儿. 可见光氧化还原催化炔基化反应的研究进展[J]. 有机化学, 2023, 43(8): 2647-2663.

Chunming Gui, Tongyao Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jin Huang, Fener Chen. Recent Advances in Visible Light Photoredox-Catalyzed Alkynylation[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2647-2663.

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图/表 47

图1. 含有炔烃结构的药物

Figure 1. Alkyne-containing pharmaceuticals

图2. 炔烃类化合物的转化

Figure 2. Transformations of alkynes

图3. 可见光氧化还原催化炔基化反应

Figure 3. Visible light photoredox-catalyzed alkynylation

图式1. 过渡金属铜活化端炔的途径

Scheme 1. Activation of terminal alkynes by transition-metal copper

图式2. 铜与光氧化还原协同催化四氢异喹啉的不对称炔基化反应

Scheme 2. Photoredox/copper dual-catalyzed asymmetric alkynylation of tetrahydroisoquinolines

图式3. 铜与光氧化还原协同催化α-氨基酸衍生的NHP酯的脱羧炔基化反应

Scheme 3. Photoredox/copper dual-catalyzed decarboxylative alkynylation of N-(acetoxy)phthalimides of α-amino acids

图式4. 可见光促进铜催化端炔与碘代烷烃的偶联

Scheme 4. Visible light-induced copper-catalyzed coupling of terminal alkynes and alkyl iodides

图式5. 可见光促进铜催化环酮肟酯、烯烃和端炔的三组分自由基偶联反应

Scheme 5. Visible light-induced copper-catalyzed radical coupling reaction of cycloketone oxime esters, alkenes, and terminal alkynes

图式6. 可见光促进铜催化芳胺、端炔和醇的多组分偶联反应

Scheme 6. Visible light-induced copper-catalyzed multicomponent coupling of arylamines, terminal alkynes and alcohols

图式7. 可见光促进铜催化脱羧炔基化反应

Scheme 7. Visible light-induced copper-catalyzed decarboxylative alkynylation

图式8. 过渡金属铜催化端炔的不对称自由基氧化C(sp3)—H/C(sp)—H交叉偶联反应

Scheme 8. Copper-catalyzed enantioselective radical oxidative C(sp3)—H/C(sp)—H cross-coupling reaction with terminal alkynes

图式9. 可见光促进铜催化环酮肟酯与端炔的C(sp)—C(sp3)偶联

Scheme 9. Visible light-induced copper-catalyzed C(sp)—C(sp3) coupling of cycloketone oxime esters and terminal alkynes

图式10. 可见光促进铜催化烯烃的双官能团化反应

Scheme 10. Visible light-induced copper-catalyzed difunctionalization of olefins

图式11. 铜与光氧化还原协同催化羧酸与端炔的脱羧炔基化反应

Scheme 11. Decarboxylative alkynylation of carboxylic acids with terminal alkynes using Cu/photoredox dual catalysis

图式12. 可见光促进铜催化远端非活化C(sp3)—H键的炔基化反应

Scheme 12. Visible light-induced copper-catalyzed alkynylation of remote unactivated C(sp3)—H bonds

图式13. 铜与光氧化还原协同催化双环[1.1.1]戊烷的自由基多组分烷基炔基化反应

Scheme 13. Radical multicomponent alkyl alkynylation of bicyclo[1.1.1]pentanes via synergistic photoredox and copper catalysis

图式14. 光氧化还原催化炔烃的三氟甲基化反应

Scheme 14. Photoredox-catalyzed trifluoromethylation of alkynes

图式15. 光氧化还原催化芳炔与多氟碘代烷烃的偶联

Scheme 15. Photoredox-catalyzed cross-coupling reactions of arylalkynes with perfluoroalkyl iodides

图式16. 光氧化还原催化EBX试剂的炔基化反应

Scheme 16. Photoredox-catalyzed alkynylation of EBX reagents

图式17. 可见光促进化学选择性的脱硼炔基化反应

Scheme 17. Visible-light-induced chemoselective deboronative alkynylation

图式18. 光氧化还原催化EBX试剂与羧酸的脱羧炔基化反应

Scheme 18. Decarboxylative alkynylation of carboxylic acids using photoredox catalysis and EBX reagents

图式19. EBX试剂在光催化炔基化反应中活性考察

Scheme 19. Investigations of EBX reagents for radical alkynylations in photoredox catalysis

图式20. 光氧化还原催化二氢吡啶与EBX试剂的C(sp)—C(sp3)偶联

Scheme 20. Photoredox catalyzed C(sp3)—C(sp) coupling of dihydropyridines and EBX reagents

图式21. 光氧化还原催化饱和氧杂环化合物或烯烃与EBX试剂的官能团化反应

Scheme 21. Photoredox catalyzed functionalization of saturated O-heterocycles or alkenes and EBX reagents

图式22. 光氧化还原催化环烷基酰胺的开环炔基化反应

Scheme 22. Photoredox catalyzed alkynylative ring-opening of cycloalkylamides

图式23. Ph-EBX试剂作光催化剂在炔基化反应中的应用

Scheme 23. Photomediated alkynylation and use of Ph-EBX reagents as photocatalyst

图式24. 光氧化还原催化远端C(sp3)—H炔基化反应

Scheme 24. Photoredox catalyzed remote C(sp3)—H alkynylation

图式25. Ar-EBX光激发促进环丙烷的炔基化反应

Scheme 25. Photoexcitation of Ar-EBX for the alkynylation of cyclopropanes

图式26. 光氧化还原金催化四氢异喹啉的炔基化反应

Scheme 26. Gold catalyzed photoredox alkynylation of tetrahydroisoquinolines

图式27. 光氧化还原金催化α-硅基叔胺与碘代炔烃的偶联

Scheme 27. Gold catalyzed photoredox cross-coupling of tertiary α-silylamines with 1-iodoalkynes

图式28. 可见光促进还原脱羧C(sp)—C(sp3)偶联反应

Scheme 28. Visible-light-induced reductive decarboxylative C(sp3)—C(sp) bond coupling reaction

图式29. 可见光促进醛的还原炔基化反应

Scheme 29. Visible light-induced reductive alkynylation of aldehydes

图式30. 可见光促进金催化的C(sp)—C(sp2)交叉偶联反应

Scheme 30. Visible light-mediated gold-catalyzed C(sp)—C(sp2) cross-coupling reaction

图式31. 可见光促进铜催化芳基磺酸盐C(sp)—C(sp2)交叉偶联

Scheme 31. Visible light-induced copper-catalyzed C(sp2)—C(sp) cross-coupling via aryl sulfonium salts

图式32. 可见光促进铜催化端炔与卤代芳烃的Sonogashira偶联

Scheme 32. Visible light-induced copper-catalyzed Sonogashira coupling of terminal alkynes and aryl halides

图式33. 可见光促进炔铜、炔酰胺和炔酯的合成

Scheme 33. Visible light-induced the synthesis of ynones, ynamides, and ynoates

图式34. 光氧化还原催化sp2 C(O)—H键炔基化反应

Scheme 34. Photoredox mediated alkynylation of sp2 C(O)—H bonds

图式35. 可见光促进钯催化端炔的双碳官能团化反应

Scheme 35. Visible light-induced palladium-catalyzed dicarbofunctionalization of terminal alkynes

图式36. 光氧化还原催化α-磷酸醇的自由基炔基化反应

Scheme 36. Photoredox catalyzed radical alkynylation of α-phosphorus alcohols

图式37. 可见光促进铜催化C(sp)—P键的形成

Scheme 37. Visible light-induced copper-catalyzed direct C(sp)—P bond formation

图式38. 可见光促进铜催化氧气氧化的C(sp)—S偶联反应

Scheme 38. Visible-light-driven copper-catalyzed aerobic oxidative C(sp)—S coupling reaction

图式39. 可见光促进铜催化C(sp)—H/Si—H交叉偶联反应

Scheme 39. Visible light-induced copper-catalyzed direct C(sp)—H/Si—H cross-coupling reaction

图式40. 铜与光氧化还原协同催化不对称炔丙基自由基氰基化反应

Scheme 40. Photoredox/copper co-catalyzed asymmetric propargylic radical cyanation

图式41. 可见光促进炔酮与三氟硼酸苄酯的交叉偶联反应

Scheme 41. Visible-light-mediated photocatalytic cross-coupling reaction of acetenyl ketones with benzyl trifluoroborate

图式42. 钯与光氧化还原协同催化炔丙基碳酸酯的炔丙基苄基化反应

Scheme 42. Photoredox/palladium co-catalyzed propargylic benzylation with propargylic carbonates

图式43. 铬与光氧化还原协同催化自由基羰基炔丙基化反应

Scheme 43. Photoredox/chromium co-catalyzed radical carbonyl propargylation

图式44. 可见光促进炔丙基溴化物的自偶联

Scheme 44. Visible light-induced homocoupling of propargyl bromides

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