羧酸酯合成酮类化合物的研究进展

doi:10.6023/cjoc202201028

摘要/Abstract

羧酸酯来源广泛, 廉价易得, 其转化受到广泛关注. 酮是一类重要的合成中间体, 可用于合成具有生物活性的复杂药物分子和功能材料. 近二十年来, 羧酸酯合成酮的研究工作取得了重要进展, 主要对近年来羧酸酯转化为酮类化合物的方法进行了综述.

Carboxylic esters are widely obtained, low-cost and readily available. Their conversions have attracted widespread attention. Ketones are important synthetic intermediates, which can be used to synthesize complicated drug molecules and functional materials with biological activity. In recent twenty years, great progress has been made in the synthesis of ketones from carboxylic esters. This review mainly covers the methods of converting carboxylic esters into ketones in recent years.

Key words: ketones, carboxylic esters, functionalization

引用此文

易文静, 孙威, 胡信全, 刘超, 靳立群. 羧酸酯合成酮类化合物的研究进展[J]. 有机化学, 2022, 42(6): 1626-1639.

Wenjing Yi, Wei Sun, Xinquan Hu, Chao Liu, Liqun Jin. Recent Advance of Ketones Synthesis from Carboxylic Esters[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1626-1639.

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图/表 38

图式1. 几种过渡金属催化羧酸酯的转化方式

Scheme 1. Several transition metal catalyzed conversions of carboxylic esters

图式2. 羧酸酯转化为酮的反应路径

Scheme 2. Reaction paths for conversion of carboxylic esters to ketones

图式3. Pd催化三氟乙酸苯酯和芳基硼酸的偶联反应

Scheme 3. Palladium-catalyzed coupling of phenyl trifluoroacetates with arylboronic acids

图式4. Pd(IPr)(cin)Cl催化苯酯的Suzuki-Miyaura偶联反应

Scheme 4. Pd(IPr)(cin)Cl catalyzed Suzuki-Miyaura coupling of carboxylic phenyl esters

图式5. Pd(IPr)(ind)Cl催化苯酯的Suzuki-Miyaura 偶联反应

Scheme 5. Pd(IPr)(ind)Cl catalyzed Suzuki-Miyaura coupling of carboxylic phenyl esters

图式6. Szostak课题组开发的Pd-NHC催化体系

Scheme 6. Pd-NHC catalytic system developed by Szostak group

图式7. Pd催化氨基酸苯酯的Suzuki-Miyaura偶联反应

Scheme 7. Palladium-catalyzed Suzuki-Miyaura coupling of phenyl ester amino acids

图式8. 硫脲钯配合物催化苯酯的Suzuki-Miyaura偶联反应

Scheme 8. Thiourea ligated palladium catalyzed Suzuki-Miyaura coupling of carboxylic phenyl esters

图式9. Pd催化苯酯与烷基硼试剂的Suzuki-Miyaura偶联反应

Scheme 9. Palladium-catalyzed Suzuki-Miyaura coupling between carboxylic phenyl esters and alkyl boranes

图式10. 五氟苯酯为底物合成酮的反应

Scheme 10. Synthesis of ketones by using pentafluorophenyl esters

图式11. Ni催化苯酯与烷基硼试剂的Suzuki-Miyaura偶联反应

Scheme 11. Nickel-catalyzed Suzuki-Miyaura coupling between carboxylic phenyl esters and alkyl boranes

图式12. Pd催化2-吡啶酯与有机硼酸的偶联反应

Scheme 12. Palladium-catalyzed coupling of 2-pyridyl esters with arylboronic acids

图式13. Pd催化三嗪酯与芳基硼酸的交叉偶联反应

Scheme 13. Palladium-catalyzed coupling of triazine esters with arylboronic acids

图式14. 非均相体系下杂芳基酯与芳基硼酸的Suzuki-Miyaura偶联反应

Scheme 14. Heterogeneous Suzuki-Miyaura coupling with heteroaryl esters and arylboronic acids

图式15. Pd催化三嗪酯与末端炔的偶联反应

Scheme 15. Palladium-catalyzed coupling of triazine esters with terminal alkynes

图式16. Ni催化苯基酯与烷基溴的还原偶联反应

Scheme 16. Nickel-catalyzed reductive coupling of carboxylic esters with alkyl bromides

图式17. Rh催化羧酸酯与芳基硼酸的偶联反应

Scheme 17. Rhodium-catalyzed coupling of carboxylic esters and arylboronic acids

图式18. Rh催化烯烃分子内的氧酰化反应

Scheme 18. Rhodium-catalyzed intramolecular oxyacylation reaction of alkenes

图式19. Ir催化烯烃分子内的氧酰化反应

Scheme 19. Iridium-catalyzed intramolecular oxyacylation reaction of alkenes

图式20. Ru3(CO)12催化2-甲基吡啶酯的反应

Scheme 20. Ru3(CO)12-catalyzed reactions of 2-pyridylmethyl esters

图式21. Cu催化羧酸酯与格氏试剂合成高烯丙酮

Scheme 21. Copper-catalyzed synthesis of homoallylic ketones with carboxylic esters and Grignard reagents

图式22. Ni催化羧酸甲酯分子内Heck型反应

Scheme 22. Nickel-catalyzed intramolecular Heck-type reactions of carboxylic methyl esters

图式23. Ni催化羧酸甲酯和烷基硼的Suzuki-Miyaura偶联反应

Scheme 23. Nickel-catalyzed Suzuki-Miyaura coupling of carboxylic methyl esters and alkyl boranes

图式24. Co催化芳基溴与氯甲酸烷基酯的偶联反应

Scheme 24. Cobalt-catalyzed coupling of aryl bromides and chloroformates.

图式25. Ni催化还原羰基化反应

Scheme 25. Ni-catalyzed reductive carbonylation

图式26. 格氏试剂与嘧啶二酯合成酮的反应

Scheme 26. Synthesis of ketones from pyrimidyl diesters and Grignard reagents

图式27. 肉桂酸酯制备β,β-二取代酮的反应

Scheme 27. Synthesis of β,β-disubstituted ketones from alkyl cinnamates

图式28. 芳基格氏试剂与三氟乙酸甲酯的三氟乙酰化反应

Scheme 28. Trifluoroacetylation of aryl Grignard reagents with methyl trifluoroacetates

图式29. 烯基格氏试剂与内酰胺酯合成高烯丙酮的反应

Scheme 29. Synthesis of homoallylic ketones from lactam esters and alkenyl Grignard reagents

图式30. 有机镁试剂与羧酸酯合成酮的连续流动反应

Scheme 30. Synthesis of ketones from carboxylic esters and organomagnesium reagents in continuous flow

图式31. 有机锂试剂与羧酸酯合成酮的连续流动反应

Scheme 31. Synthesis of ketones from carboxylic esters and organolithum reagents in continuous flow

图式32. 有机锂试剂与酯合成2-吡啶酮的连续流动反应

Scheme 32. Synthesis of 2-pyridyl ketones from 2-lithiopyridines with carboxylic esters in continuous flow

图式33. 羧酸酯的亲核三氟甲基化反应

Scheme 33. Nucleophilic trifluoromethylation of carboxylic esters

图式34. 羧酸酯与偕二硼酸酯脱质子的加成反应

Scheme 34. Deprotonative addition of gem-diboronates with carboxylic esters

图式35. 路易斯碱活化的苄基偕二硼与羧酸酯反应合成酮类化合物

Scheme 35. Synthesis of ketones from Lewis base activated benzyl gem-diboronates with carboxylic esters

图式36. 芳烃与羧酸酯合成酮的反应

Scheme 36. Synthesis of ketones from arenes and carboxylic esters

图37. 光诱导氮卡宾催化羧酸酯的烷基化反应

Scheme 37. NHC-catalyzed alkylation of carboxylic esters via direct Photoexcitation

图式38. 光/镍协同催化2-吡啶酯与NHPI酯的还原偶联反应

Scheme 38. Nickel/Photoredox dual-catalyzed reductive coupling of 2-pyridyl esters with NHPI esters

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