不对称羰基化偶联反应研究进展

doi:10.6023/cjoc202409024

有机化学 ›› 2025, Vol. 45 ›› Issue (6): 2007-2047.DOI: 10.6023/cjoc202409024 上一篇下一篇

综述与进展

不对称羰基化偶联反应研究进展

苏雷^a^,^b^,^†, 杨熙^a^,^b^,^†, 闫捷^c^,^*(), 蒋元力^c^,^d^,^*(), 陈丽娟^b, 郑庆舒^a^,^b^,^*(), 刘家旺^a^,^b^,^*()

^a 上海交通大学变革性分子前沿科学中心上海市手性药物分子工程重点实验室上海 200240
^b 上海交通大学化学化工学院上海 200240
^c 河南能源化工集团有限公司郑州 450046
^d 郑州大学化工学院郑州 450001

收稿日期:2024-09-20 修回日期:2024-11-14 发布日期:2024-12-26
通讯作者: 闫捷, 蒋元力, 郑庆舒, 刘家旺
作者简介:
^†共同第一作者.
基金资助:
国家重点研发计划(2023YFA1507500); 国家自然科学基金(22201173); 中央高校基础科研项目(23X010301599); 中央高校基础科研项目(23X010302490); 中央高校基础科研项目(24X010301678); 河南能源化工集团有限公司(22H010101930); 上海市青年科技启明星计划(21QA1404900)

Recent Advances in Asymmetric Carbonylative Cross-Coupling Reactions

Lei Su^a^,^b^,^†, Xi Yang^a^,^b^,^†, Jie Yan^c^,^*(), Yuanli Jiang^c^,^d^,^*(), Lijuan Chen^b, Qingshu Zheng^a^,^b^,^*(), Jiawang Liu^a^,^b^,^*()

^a Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240
^b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
^c Henan Energy Chemical Group Co., Ltd., Zhengzhou 450046
^d School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001

Received:2024-09-20 Revised:2024-11-14 Published:2024-12-26
Contact: Jie Yan, Yuanli Jiang, Qingshu Zheng, Jiawang Liu
About author:
^†The authors contributed equally to this work.
Supported by:
National Key R&D Program of China(2023YFA1507500); National Natural Science Foundation of China(22201173); Fundamental Research Funds for the Central Universities(23X010301599); Fundamental Research Funds for the Central Universities(23X010302490); Fundamental Research Funds for the Central Universities(24X010301678); Henan Energy Chemical Group Co., Ltd(22H010101930); Shanghai Rising-Star Program(21QA1404900)

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摘要/Abstract

手性羰基化合物广泛存在于天然产物和药物中, 同时它们也是重要的有机合成中间体. 过渡金属催化的不对称羰基化偶联反应是合成酯、酰胺、酮和硫酯等手性羰基化合物最直接高效的方法之一. 此综述总结了近十年来不对称羰基化偶联反应领域的研究进展, 主要包括酰基金属中间体与含氧、氮、碳和硫的亲核试剂或亲电试剂反应的不对称羰基化偶联反应.

关键词: 羰化反应, 过渡金属催化, 不对称催化, 一氧化碳, 偶联反应

Chiral carbonyl compounds frequently occur in natural products and pharmaceuticals. Additionally, they serve as important intermediates in organic synthesis. Transition metal-catalyzed asymmetric carbonylative cross-coupling reactions are among the most straightforward and effective methods for synthesizing chiral carbonyl compounds, including esters, amides, and ketones. The advances in asymmetric carbonylative cross-coupling reactions using various O-, N-, C-, and S-containing nucleophiles or electrophiles over the past decade are summarized.

Key words: carbonylation, transition-metal catalysis, asymmetric catalysis, carbon monoxide, cross-coupling reaction

引用此文

苏雷, 杨熙, 闫捷, 蒋元力, 陈丽娟, 郑庆舒, 刘家旺. 不对称羰基化偶联反应研究进展[J]. 有机化学, 2025, 45(6): 2007-2047.

Lei Su, Xi Yang, Jie Yan, Yuanli Jiang, Lijuan Chen, Qingshu Zheng, Jiawang Liu. Recent Advances in Asymmetric Carbonylative Cross-Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 2007-2047.

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图/表 64

Scheme 1. Pd-catalyzed asymmetric intramolecular Heck-Matsuda carbonylation of arenediazonium salts

Scheme 2. Pd-catalyzed asymmetric intramolecular cyclization/carbonylative esterification

Scheme 3. Pd-catalyzed asymmetric tandem Heck/carbonylative desymmetrization of cyclopentenes

Scheme 4. Pd-catalyzed asymmetric intramolecular cyclization/carbonylative esterification of carbamoyl chloride tethered alkenes

Scheme 5. Pd-catalyzed asymmetric 7-exo-trig Heck carbonylation cascade reaction

Scheme 6. Pd-catalyzed asymmetric cyclization/carbonylation of propargyl alcohol derivatives

Scheme 7. Pd-catalyzed asymmetric intramolecular cyclization/carbonylation of aryl iodides

Scheme 8. Pd-catalyzed asymmetric C—C bond activation/carbonylation of aryl iodides

Scheme 9. Pd-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes

Scheme 10. Pd-catalyzed asymmetric hydroesterification of β-carbonyl functionalized alkenes

Scheme 11. Pd-catalyzed asymmetric hydroesterification of α-carboxylic alkenes

Scheme 12. Pd-catalyzed asymmetric hydroesterification of styrenes

Scheme 13. Pd-catalyzed asymmetric hydroesterification of vinylarenes with phenols as nucleophiles

Scheme 14. Pd-catalyzed asymmetric tandem Heck/carbonylative desymmetrization of cyclopentenes with phenols

Scheme 15. Pd-catalyzed asymmetric intramolecular hydroesterification of styrenes or tertiary alcohols

Scheme 16. Pd-catalyzed asymmetric intramolecular Heck/carbonylation of aryl bromides modified by bisallyl-phosphine oxides

Scheme 17. Pd-catalyzed asymmetric sequential cyclization and carbonylation of 1,6-enynes with phenols as nucleophiles

Scheme 18. Pd-catalyzed asymmetric hydroesterification of styrenes with phenyl formate

Scheme 19. Pd-catalyzed asymmetric carbonylative esterification of aryl iodides with phenyl formate

Scheme 20. Ni-catalyzed asymmetric hydroesterification of cyclopropenes with phenyl formate

Scheme 21. Pd-catalyzed asymmetric carboxylation of propargylic alcohols via kinetic resolution

Scheme 22. Pd-catalyzed asymmetric hydrocarboxylation of styrenes

Scheme 23. Pd-catalyzed asymmetric hydrocarboxylation of β-carbonyl functionalized alkenes

Scheme 24. Pd-catalyzed asymmetric double hydroxycarbonylation of terminal alkynes

Scheme 25. Pd-catalyzed asymmetric intramolecular Heck carbonylation of o-iodoacrylanilides

Scheme 26. Pd-catalyzed asymmetric oxyesterification of alkenes

Scheme 27. Pd-catalyzed asymmetric oxyesterification of alkenes

Scheme 28. Pd-catalyzed asymmetric intramolecular cyclization/aminocarbonylation

Scheme 29. Pd-catalyzed heck carbonylation enabled by monodentate ligand

Scheme 30. Pd-catalyzed asymmetric tandem Heck/aminocarbonylation via desymmetrization of cyclopentenes

Scheme 31. Pd-catalyzed asymmetric cascade 7-exo-trig Heck/carbonylation reaction

Scheme 32. Pd-catalyzed asymmetric tandem Heck/carbonylation

Scheme 33. Pd/Cu catalyzed enantioselective desymmetric C—H aminocarbonylation

Scheme 34. Pd-catalyzed asymmetric C(sp2)—H activation and carbonylation of N-alkoxy-2,2-diarylpropanamides

Scheme 35. Pd-catalyzed enantioselective C(sp3)—H functionalization of cyclopropylmethylamines

Scheme 36. Enantioselective kinetic resolution of sterically hindered benzylamines

Scheme 37. Cobalt-catalyzed enantioselective C—H carbonylation

Scheme 38. Pd-catalyzed asymmetric Markovnikov hydroaminocarbonylation of alkenes

Scheme 39. Pd-catalyzed asymmetric hydroaminocarbonylation of alkynes

Scheme 40. Pd-catalyzed asymmetric migratory hydroaminocarbonylation of alkenes

Scheme 41. Pd-catalyzed atroposelective carbonylation of aryl iodides

Scheme 42. Pd-catalyzed atroposelective ring-opening carbonylation reaction of cyclic diarylsulfonium salts

Scheme 43. Pd-catalyzed asymmetric double carbonylation of diaryliodonium salt

Scheme 44. Pd-catalyzed enantioselective carbonylation of sulfonimidamide

Scheme 45. Pd-catalyzed dynamic kinetic asymmetric aminocarbonylation

Scheme 46. Copper-catalyzed asymmetric carbonylative hydroamidation of styrenes to branched amides

Scheme 47. Copper-catalyzed asymmetric carbonylative synthesis of β-boryl amides

Scheme 48. Copper-catalyzed asymmetric hydroaminocarbonylation toward α-chiral secondary amides

Scheme 49. Copper-catalyzed asymmetric hydroaminocarbonylation toward β-chiral amides

Scheme 50. Copper-catalyzed asymmetric hydroaminocarbonylation of non-activated internal olefins

Scheme 51. Copper-catalyzed asymmetric reductive relay hydroaminocarbonylation toward γ-chiral amides

Scheme 52. Pd-catalyzed oxidative cascade carbonylation-carbocyclization reaction of enallenes

Scheme 53. Pd-catalyzed asymmetric intramolecular Heck/carbonylative C—C cross coupling

Scheme 54. Pd-catalyzed heck carbonylation enabled by monodentate ligand

Scheme 55. Pd-catalyzed asymmetric carbonylative heck reaction of o-iodoanilines with allenes

Scheme 56. Pd-catalyzed enantioselective α-carbonylative arylation

Scheme 57. Pd-catalyzed asymmetric C—C bond activation/carbonylative of aryl iodides with arylboronic acid

Scheme 58. Pd/Cu catalyzed enantioselective intramolecular Heck and carbonylative C—C cross-coupling reactions

Scheme 59. Enantioselective Pd-catalyzed carbonylative heck esterification of o-iodoalkenylbenzenes

Scheme 60. Three-component asymmetric reductive carbonylation of alkenes

Scheme 61. Enantioselective Pd-catalyzed carbonyl alkynylation

Scheme 62. Pd-catalyzed asymmetric tandem carbonylation-Heck reaction of cyclopentenes

Scheme 63. Pd-catalyzed asymmetric thiocarbonylation of styrenes

Scheme 64. Ni-catalyzed asymmetric thiocarbonylation of cyclopropenes

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不对称羰基化偶联反应研究进展

Recent Advances in Asymmetric Carbonylative Cross-Coupling Reactions

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