Nickel and Cobalt-Catalyzed Asymmetric Reductive Coupling of Halides with Aldehydes, Ketones and Imines

doi:10.6023/cjoc202412018

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 1946-1960.DOI: 10.6023/cjoc202412018 Previous Articles Next Articles

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镍和钴催化卤代烃与醛酮/亚胺的还原偶联反应研究进展

田江艳^a, 李驰^a, 陈剑飞^c, 吕辉^a^,^b^,^c^,^d^,^*()

^a 武汉大学化学与分子科学学院生物医用高分子材料教育部重点实验室武汉 430072
^b 武汉大学化学与分子科学学院有机硅化合物及材料教育部工程中心武汉 430072
^c 武汉大学电网环境保护国家重点实验室武汉 430072
^d 武汉大学有机高分子光电功能材料湖北省重点实验室武汉 430072

收稿日期:2024-12-20 修回日期:2025-01-27 发布日期:2025-03-07
通讯作者: 吕辉
基金资助:
国家自然科学基金(22071188); 国家自然科学基金(22371217)

Nickel and Cobalt-Catalyzed Asymmetric Reductive Coupling of Halides with Aldehydes, Ketones and Imines

Jiangyan Tian^a, Chi Li^a, Jianfei Chen^c, Hui Lv^a^,^b^,^c^,^d^,^*()

^a Key Laboratory of Biomedical Polymers of Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
^b Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
^c State Key Laboratory of Power Grid Environmental Protection, Wuhan University, Wuhan 430072
^d Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, Wuhan University, Wuhan 430072

Received:2024-12-20 Revised:2025-01-27 Published:2025-03-07
Contact: Hui Lv
Supported by:
National Natural Science Foundation of China(22071188); National Natural Science Foundation of China(22371217)

The transition metal-catalyzed reductive coupling of halides with aldehydes, ketones and imines is one of the most attractive and well-established methods for preparing alcohols and amines, which avoids the use of stoichiometric quantities of organometallic reagents and organoboron reagents, and has higher atomic economy and step economy. Very recently, some breakthroughs have been made in nickel and cobalt-catalyzed reductive coupling of halides with aldehydes, ketones and imines, capturing the attention of chemists and becoming a hot topic in organic synthesis. Thus, the recent progress in nickel and cobalt-catalyzed reductive coupling of halides with aldehydes, ketones, and imines is reviewed.

Key words: nickel, cobalt, aldehydes, ketones, imines, reductive coupling

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Jiangyan Tian, Chi Li, Jianfei Chen, Hui Lv. Nickel and Cobalt-Catalyzed Asymmetric Reductive Coupling of Halides with Aldehydes, Ketones and Imines[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1946-1960.

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Fig. & Tab. 35

Scheme 1. Ni/Co-catalyzed reductive coupling of halides toward carbonyls and imines

Scheme 2. Nickel-catalyzed reductive arylation of aldehydes

Scheme 3. Reductive arylation of aromatic aldehydes

Scheme 4. Reductive arylation of aldehydes

Scheme 5. Reformatsky addition

Scheme 6. Reductive allylation of aldehydes

Scheme 7. Reductive alkylation of aliphatic aldehydes

Scheme 8. Reductive arylation of aldehydes

Scheme 9. Reductive arylation of aldehydes

Scheme 10. Nickel/photoredox dual-catalyzed reductive arylation of aldehydes

Scheme 11. Reductive cyclization of α-ketoamides and β-keto-amides

Scheme 12. Asymmetric reductive arylation of aldehydes

Scheme 13. Asymmetric reductive arylation of aldehydes

Scheme 14. Asymmetric reductive arylation of aldehydes

Scheme 15. Asymmetric reductive alkenylation of aldehydes

Scheme 16. Asymmetric reductive arylation of aldehydes

Scheme 17. Reductive cyclization of α-ketoamides

Scheme 18. Asymmetric reductive cyclization of ketones

Scheme 19. Desymmetrizative cyclization of ketones

Scheme 20. Asymmetric reductive arylation of ketones

Scheme 21. Reductive alkylation of imines

Scheme 22. Asymmetric reductive alkylation of imines

Scheme 23. Asymmetric reductive arylation of imines

Scheme 24. Asymmetric reductive arylation of aldehydes

Scheme 25. Reductive arylation of aromatic aldehydes

Scheme 26. Asymmetric reductive alkenylation of aldehydes

Scheme 27. Asymmetric reductive alkenylation and arylation of aldehydes

Scheme 28. Asymmetric reductive alkenylation and arylation of aldehydes

Scheme 29. Proposed mechanism for reductive arylation of aldehydes

Scheme 30. Reductive arylation of aldehydes

Scheme 31. Asymmetric reductive alkylation of ketones

Scheme 32. Reductive arylation of imines

Scheme 33. Asymmetric reductive arylation of imines

Scheme 34. Asymmetric reductive alkenylation of imines

Scheme 35. Asymmetric reductive alkylation of imines

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镍和钴催化卤代烃与醛酮/亚胺的还原偶联反应研究进展

Nickel and Cobalt-Catalyzed Asymmetric Reductive Coupling of Halides with Aldehydes, Ketones and Imines

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Fig. & Tab. 35

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