机械化学条件下C—H键官能化反应研究进展

doi:10.6023/cjoc202106046

摘要/Abstract

机械力化学近年来获得广泛关注. 利用机械力促进的C—H键官能化反应的报道也日趋增多, 正在成为一个新兴的研究热点. 与传统的溶剂中进行的有机反应相比, 机械力促进的有机反应通常反应时间较短且无需溶剂, 更符合绿色合成的要求. 值得注意的是, 基于机械化学出色的性能和潜力, 一些传统合成方法中长期存在的问题也能通过机械化学方法得以解决. 因此, 及时对该领域进行总结将有助于化学工作者全面了解其发展现状, 并促进发展更高效的机械化学合成方法. 综述了近几年来机械力促进的碳氢键官能化反应研究进展及合成应用, 并对该领域存在的局限性和发展前景进行分析和展望.

关键词: 机械化学, C—H键官能化, 球磨技术, 无溶剂, 绿色化学

Mechanochemistry has received increasing attention in the past decade. Among which, the mechanochemical C—H bond functionalization has emerged as a hot research topic. In comparison with the traditional solution-based organic reactions, the mechanochemical transformation features solvent-less conditions and short reaction time, constituting a green and efficient synthetic method in the modern chemical society. Notably, given the outstanding features, some long-standing challenges in the previous solution-based reactions could be well-solved by mechanochemical methods. Therefore, a timely comprehensive overview to recognize the present status of the mechanochemical C—H bond functionalization is of great importance to stimulate the development of more efficient synthetic methods. In this review, the state of the art for mechanochemical C—H bond transformation is presented. The limitation in this research field is also analyzed and the outlook of this area is prospected.

Key words: mechanochemistry, C—H bond functionalization, ball milling, solvent-free, green chemistry

引用此文

周琨, 毛羊杰, 吴峰伟, 娄绍杰, 许丹倩. 机械化学条件下C—H键官能化反应研究进展[J]. 有机化学, 2021, 41(12): 4623-4638.

Kun Zhou, Yangjie Mao, Fengwei Wu, Shaojie Lou, Danqian Xu. Recent Advances in C—H Bond Functionalization under Mechanochemical Conditions[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4623-4638.

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图/表 43

图1. 机械力促进的C—H键官能化反应论文数量(2011~2020)

Figure 1. Number of peer-reviewed papers on mechanochemical C—H bond functionalization (2011~2020)

图式1. 机械化学条件下偶氮苯的固态C—H键活化

Scheme 1. Mechanochemical solid-state C—H bond activation of azobenzenes

图式2. 机械力促进合成芳基金配合物

Scheme 2. Mechanosynthesis of aryl-Au complexes

图式3. 机械力促进铑催化乙酰苯胺C—H键烯基化反应

Scheme 3. Mechanochemical Rh catalyzed C—H bond olefination of acetanilides

图式4. 机械力促进选择性合成3-烯基吲哚和β,β-二吲哚基丙酸酯

Scheme 4. Mechanochemical selective synthesis of 3-vinylindoles or β,β-diindolyl propionates

图式5. 机械力促进3-烯基吲哚和β,β-二吲哚基丙酸酯选择性合成的可能反应机理

Scheme 5. Proposed mechanism of mechanochemical selective synthesis of 3-vinylindoles and β,β-diindolyl propionates

图式6. 机械力促进呋喃或噻吩的烯基化反应

Scheme 6. Mechanochemical alkenylation of furans or thiophenes

图式7. 机械力促进吲唑的烯基化和杂芳基化反应

Scheme 7. Mechanochemical alkenylation and heteroarylation of indazoles

图式8. 机械化学合成CFI-400945中间体和YC-1

Scheme 8. Mechanosynthesis of an intermediate of CFI-400945 and YC-1

图式9. 机械力促进锰催化吲哚C—H键烯基化反应

Scheme 9. Mechanochemical Mn catalyzed C—H bond alkenylation of indoles

图式10. 机械力促进吲哚选择性C—H键炔基化反应

Scheme 10. Mechanochemical selective C—H bond alkynylation of indoles

图式11. 机械力促进钯催化交叉脱氢偶联芳基化反应

Scheme 11. Mechanochemical Pd catalyzed cross dehydrogenation coupling arylation

图式12. 机械力促进钯催化的C—H键芳基化反应KIE实验

Scheme 12. KIE experiments for mechanochemical Pd catalyzed C—H bond arylations

图式13. 机械力促进Pd催化的吲哚C—H键芳基化反应

Scheme 13. Mechanochemical Pd catalyzed C—H bond arylation of indoles

图式14. 机械力促进钴催化吲哚C—H键烯丙基化反应

Scheme 14. Mechanochemical Co catalyzed C—H bond allylation of indoles

图式15. 机械力促进铑催化的C—H键甲基化反应

Scheme 15. Mechanochemical Rh catalyzed C—H bond methylation

图式16. 机械力促进铜催化吲哚与α-酮酸酯的脱羧酰化反应

Scheme 16. Mechanochemical Cu catalyzed decarboxylative acylation of indoles with α-ketonates

图式17. 机械力促进铜催化交叉脱氢偶联反应

Scheme 17. Mechanochemical Cu catalyzed CDC reaction

图式18. 机械力促进四氢异喹啉C(sp3)—H键不对称交叉脱氢偶联反应

Scheme 18. Mecheanochemical asymmetric C(sp3)—H CDC reaction of tetrahydroisoquinolines

图式19. 机械力促进铱催化的C—H键磺酰胺化反应

Scheme 19. Mechanochemical Ir catalyzed C—H bond sulfonamidation

图式20. 机械力促进铑催化的C—H键与二噁唑酮的酰胺化反应

Scheme 20. Mechanochemical Rh catalyzed C—H bond amidation with oxazolidinediones

图式21. 机械力促进钴催化的C—H键酰胺化反应

Scheme 21. Mechanochemical Co catalyzed C—H bond amidation

图式22. 机械力促进钴催化二茂铁的C—H键酰胺化反应

Scheme 22. Mechanochemical Co catalyzed ferrocene C—H bond amidation

图式23. 机械力促进铑催化N-亚硝基苯胺的邻位酰胺化反应

Scheme 23. Mechanochemical Rh-catalyzed C—H bond amidation of N-nitrosoanilines

图式24. 机械力促进铑催化的C(sp3)—H键胺化反应

Scheme 24. Mechanochemical Rh-catalyzed C(sp3)—H bond amination

图式25. 机械力促进铑催化2-苯基吡啶的卤化反应

Scheme 25. Mechanochemical Rh-catalyzed halogenation of 2-phenylpyridine

图式26. 机械力促进钯催化C—H键碘代反应

Scheme 26. Mechanochemical Pd catalyzed C—H bond iodination

图式27. 机械力化学促进C—H键碘化反应可能的反应机理

Scheme 27. Plausible mechanism of the mechanochemical C—H bond iodination

图式28. 机械力促进铱催化C—H键硼基化反应

Scheme 28. Mechanochemical Ir-catalyzed C—H bond borylation

图式29. 机械力促进钯催化C—H键醚化反应

Scheme 29. Mechanochemical Pd catalyzed C—H bond etherification

图式30. 机械力促进噻唑衍生物与有机磷化合物的交叉偶联反应

Scheme 30. Mechanochemical cross-coupling reactions of thiazoles with organophosphorus compounds

图式31. 机械力促进铑催化合成吲哚

Scheme 31. Mechanochemical synthesis of indoles under Rh catalysis

图式32. 机械力促进铱催化磺酰亚胺环化生成1,2-苯并噻嗪衍生物

Scheme 32. Mechanochemical synthesis of 1,2-benzothiazines from sulfonimidamides under Ir catalysis

图式33. 醛和N-氯胺的酰胺化反应的不同策略

Scheme 33. Amidation of aldehydes with N-chloramines under neat conditions or ball milling conditions

图式34. 醛与N-氯胺的偶联生成酰胺的反应机理

Scheme 34. Proposed mechanism for the amide formation from aldehyde and N—Cl amine

图式35. 机械力促进的醛和胺的酰胺化反应

Scheme 35. Mechanochemical synthesis of amides from aldehydes and amines

图式36. 过渡金属/光催化自由基碳氢键官能化

Scheme 36. Radical C—H functionalization under transition metal catalysis or photocatalysis

图式37. 机械-氧化还原实现杂环化合物的C—H键芳基化

Scheme 37. Mechano-redox C—H bond arylation of heterocycles

图式38. 使用压电材料实现机械力-氧化还原固态自由基C—H键三氟甲基化反应

Scheme 38. Mechanochemical solid-state radical C—H bond trifluoromethylation in the presence of piezoelectric materials

图式39. 不同条件下C—H键自由基三氟甲基化反应比较

Scheme 39. Radical C—H bond trifluoromethylation under different conditions

图式40. 机械力-氧化还原三氟甲基化的控制实验

Scheme 40. Control experiments in the mechano-redox C—H bond trifluoromethylation

图式41. 机械力促进I2催化吲哚与二硫化物的C—H键硫基化反应

Scheme 41. Mechanochemical I2 catalyzed C—H bond sulfuration of indoles with disulfides

图式42. 机械力促进芳基化合物的C—H键硫氰化反应

Scheme 42. Mechanochemical aryl C—H bond thiocyanation

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