可见光催化的Minisci反应研究进展

doi:10.6023/cjoc202104024

摘要/Abstract

氮杂芳环广泛存在于天然产物、药物分子、有机材料及配体中. 通过选择性碳氢键官能团化的方式对氮杂芳环进行后期修饰具有重要意义. 在酸性和氧化条件下, 烷基自由基对氮杂芳环的加成反应, 即Minisci反应, 提供了一种合成烷基取代的含氮芳环的方法. 传统的Minisci反应往往需要过量的氧化剂、酸以及高温, 这大大限制了底物的适用范围. 随着光催化在有机合成中的快速发展, 近几年来多种光催化的Minisci反应被报道, 并被成功应用到药物的合成中. 对近年来可见光催化的Minisci反应进行了概述.

关键词: 含氮芳环, Minisci反应, 烷基自由基, 光催化

N-Heteroarenes are present in a wide variety of natural products, small-molecule drugs, organic materials, and ligands. Therefore, the methods for selective C—H functionalization of N-heteroarenes are highly sought-after for late-stage modification of pharmaceuticals. A useful tool for the synthesis of alkyl-substituted nitrogen-containing aromatic rings is the Minisci reaction, in which a protonated N-heteroarene is attacked by an alkyl radical under oxidative and acidic conditions. Classic Minisci reactions often require the use of excess oxidant, excess acid, and high temperature, which greatly limits the scope of the substrates. With the rapid development of photocatalysis in organic synthesis, in recent years, a variety of photocatalytic Minisci reactions have been reported, and successfully been applied to the synthesis of drugs. In this paper, the visible light mediated Minisci reactions in recent years are briefly reviewed.

Key words: N-heteroarenes, Minisci reaction, alkyl radical, photocatalysis

引用此文

董建洋, 刘玉秀, 汪清民. 可见光催化的Minisci反应研究进展[J]. 有机化学, 2021, 41(10): 3771-3791.

Jianyang Dong, Yuxiu Liu, Qingmin Wang. Recent Advances in Visible-Light-Mediated Minisci Reactions[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3771-3791.

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图/表 48

图式1. 可见光催化的Minisci反应

Scheme 1. Visible-light-mediated Minisci reactions

图式2. 可见光催化的烷基羧酸脱羧的Minisci反应

Scheme 2. Visible-light-mediated decarboxylative Minisci reaction with alkyl carboxylic acids

图式3. 可见光催化的喹喔啉酮的酰基化反应

Scheme 3. Visible-light-mediated acylation of quinoxalin- 2(1H)-ones

图式4. 可见光催化的芳基羧酸的Minisci反应

Scheme 4. Visible-light-mediated Minisci reaction with aryl carboxylic acids

图式5. 可见光催化的活性羧酸酯的Minisci反应

Scheme 5. Visible-light-mediated Minisci reaction with activated esters

图式6. 可见光催化的活性羧酸酯的不对称Minisci反应

Scheme 6. Visible-light-mediated enantioselective Minisci reaction with activated esters

图式7. 铜催化剂的活性羧酸酯的Minisci反应

Scheme 7. Cu-catalyzed Minisci reaction with activated esters

图式8. 光催化下三苯基膦/碘化钠介导的活性羧酸酯的Minisci反应

Scheme 8. Photocatalytic Minisci reaction with activated esters mediated by triphenylphosphine and sodium iodide

图式9. 可见光催化的酰氯的Minisci反应

Scheme 9. Visible-light-mediated Minisci reaction with acid chloride

图式10. 可见光催化的醚类化合物的Minisci反应

Scheme 10. Visible-light-mediated Minisci reaction with ethers

图式11. 苯甲醛介导的HAT过程的Minisci反应

Scheme 11. Benzaldehyde-mediated Minisci reaction via HAT process

图式12. 可见光催化的无需光催化剂的醚类化合物的Minisci反应

Scheme 12. Visible-light-mediated Minisci reaction with ethers under photocatalyst-free conditions

图式13. 可见光催化的无需光催化剂的醛的Minisci反应

Scheme 13. Visible-light-mediated Minisci reaction with aldehydes under photocatalyst-free conditions

图式14. 可见光催化的无需光催化剂的烷烃的Minisci反应

Scheme 14. Visible-light-mediated Minisci reaction with alkanes under photocatalyst-free conditions

图式15. 可见光催化的甲醇的Minisci反应

Scheme 15. Visible-light-mediated Minisci reaction with methanol

图式16. 可见光催化的硅烷的Minisci反应

Scheme 16. Visible-light-mediated Minisci reaction with silanes

图式17. 可见光催化的胺类化合物的Minisci反应

Scheme 17. Visible-light-mediated Minisci reaction with amines

图式18. 可见光催化的氧气氧化的醛的Minisci反应

Scheme 18. Visible-light-mediated Minisci reaction with aldehydes using O2 as the oxidant

图式19. 光催化下氮/氧自由基介导的烷烃的Minisci反应

Scheme 19. Photocatalytic Minisci reaction with alkanes mediated by N/O-centered radical

图式20. (Bu4N)4[W10O32]催化的烷烃的Minisci反应

Scheme 20. (Bu4N)4[W10O32]-catalyzed Minisci reaction with alkanes

图式21. 可见光催化的亚甲基选择性的Minisci反应

Scheme 21. Visible-light-mediated Minisci reaction with highly selectivity of methylene

图式22. 可见光催化的酰胺的不对称Minisci反应

Scheme 22. Visible-light-mediated enantioselective Minisci reaction with amides

图式23. 可见光催化的醇分子内1,5氢迁移的Minisci反应

Scheme 23. Visible-light-mediated Minisci reaction with alcohols via 1,5-hydrogen-atom-transfer

图式24. 可见光催化的酰胺分子内1,5氢迁移的Minisci反应

Scheme 24. Visible-light-mediated Minisci reaction with amides via 1,5-hydrogen-atom-transfer

图式25. 可见光催化的活化的酰胺分子内1,5氢迁移的Minisci反应

Scheme 25. Visible-light-mediated Minisci reaction with activated-amides via 1,5-hydrogen-atom-transfer

图式26. 可见光催化的烷基硼酸的Minisci反应

Scheme 26. Visible-light-mediated Minisci reaction with alkyl boronic acids

图式27. 可见光催化的氧气氧化的烷基硼酸的Minisci反应

Scheme 27. Visible-light-mediated Minisci reaction with alkyl boronic acids using O2 as the oxidant

图式28. 可见光催化的烷基三氟硼酸钾的Minisci反应

Scheme 28. Visible-light-mediated Minisci reaction with alkyl trifluoroborate salts

图式29. 光电协同催化的烷基三氟硼酸钾的Minisci反应

Scheme 29. Photoelectrochemical Minisci reaction with alkyl trifluoroborate salts

图式30. 可见光催化的三氟甲烷磺酰氯的Minisci反应

Scheme 30. Visible-light-mediated Minisci reaction with triflyl chloride

图式31. 可见光催化的氧气氧化的二氟甲基亚磺酸钠的Minisci反应

Scheme 31. Visible-light-mediated Minisci reaction with sodium difluoromethane sulfonate using O2 as the oxidant

图式32. [Au2(dppm)2]Cl2催化的溴代烷烃的Minisci反应

Scheme 32. [Au2(dppm)2]Cl2-catalyzed Minisci reaction with alkyl bromides

图式33. Mn2(CO)10催化的烷基碘的Minisci反应

Scheme 33. Mn2(CO)10-catalyzed Minisci reaction with alkyl iodides

图式34. 可见光催化的烷基碘的Minisci反应

Scheme 34. Visible-light-mediated Minisci reaction with alkyl iodides

图式35. 可见光催化的t-BPA作氧化剂的烷基碘的Minisci反应

Scheme 35. Visible-light-mediated Minisci reaction with alkyl iodides using t-BPA as the oxidant

图式36. 可见光催化通过卤原子转移的Minisci反应

Scheme 36. Visible-light-mediated Minisci reaction via halogen atom transfe

图式37. 生物体中的自旋中心迁移(SCS)过程

Scheme 37. Spin-centre shift (SCS) process in organism

图式38. 可见光催化的一级醇的Minisci反应

Scheme 38. Visible-light-mediated Minisci reaction with primary alcohol

图式39. 紫外光照射下甲醇的Minisci甲基化反应

Scheme 39. Minisci methylation reaction with methanol under UV light

图式40. 可见光催化的羰基化合物脱氧的Minisci反应

Scheme 40. Visible-light-mediated deoxygenation Minisci reaction with carbonyl compounds

图式41. 可见光催化的醛的Minisci羟烷基化反应

Scheme 41. Visible-light-mediated Minisci hydroxyalkylation with aldehydes

图式42. 可见光催化的过氧化物碳碳键断裂的Minisci反应

Scheme 42. Visible-light-mediated Minisci reaction via peroxide fragmentation

图式43. 可见光催化的醇β-裂解的Minisci反应

Scheme 43. Visible-light-mediated Minisci reaction with alcohols via β-scission

图式44. 可见光催化的芳基重氮盐的Minisci反应

Scheme 44. Visible-light-mediated Minisci reaction with aryl diazonium salts

图式45. 可见光催化的烷基二氢吡啶的Minisci反应

Scheme 45. Visible-light-mediated Minisci reaction with alky-dihydropyridine

图式46. 可见光催化的烷基吡啶盐的Minisci反应

Scheme 46. Visible-light-mediated Minisci reaction with alkylpyridinium salts

图式47. 烯烃参与的三组分Minisci反应

Scheme 47. Three-component Minisci reaction with alkenes

图式48. 可见光催化的有机磷和烯烃三组分Minisci反应

Scheme 48. Visible-light-mediated three-component Minisci reaction with phosphines and alkene

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