镍和钴催化卤代烃与醛酮/亚胺的还原偶联反应研究进展

doi:10.6023/cjoc202412018

有机化学 ›› 2025, Vol. 45 ›› Issue (6): 1946-1960.DOI: 10.6023/cjoc202412018 上一篇下一篇

综述与进展

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)

文章分享

摘要/Abstract

过渡金属催化卤代烃与醛酮/亚胺的还原偶联反应可以避免化学计量的有机金属试剂与硼试剂的使用, 并且操作简单, 原子经济性好, 是合成醇和胺最理想的方法之一. 近几年来, 镍和钴催化卤代物与醛酮/亚胺的还原偶联反应引起广泛关注并取得较大的进展, 成为有机化学的研究热点之一. 该综述对镍和钴催化卤代物与醛酮/亚胺的还原偶联反应研究进展进行了系统总结.

关键词: 镍, 钴, 醛, 酮, 亚胺, 还原偶联

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

引用此文

田江艳, 李驰, 陈剑飞, 吕辉. 镍和钴催化卤代烃与醛酮/亚胺的还原偶联反应研究进展[J]. 有机化学, 2025, 45(6): 1946-1960.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 35

图式1. 镍/钴催化卤代烃与醛酮/亚胺的还原偶联

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

图式2. 镍催化醛的还原芳基化

Scheme 2. Nickel-catalyzed reductive arylation of aldehydes

图式3. 芳基醛的还原芳基化

Scheme 3. Reductive arylation of aromatic aldehydes

图式4. 醛的还原芳基化

Scheme 4. Reductive arylation of aldehydes

图式5. Reformatsky加成

Scheme 5. Reformatsky addition

图式6. 醛的还原烯丙基化

Scheme 6. Reductive allylation of aldehydes

图式7. 醛的还原烷基化

Scheme 7. Reductive alkylation of aliphatic aldehydes

图式8. 醛的还原芳基化

Scheme 8. Reductive arylation of aldehydes

图式9. 醛的还原芳基化

Scheme 9. Reductive arylation of aldehydes

图式10. 光协同镍催化醛的还原芳基化

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

图式 11. α-酮酰胺和β-酮酰胺的还原环化

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

图式12. 醛的不对称还原芳基化

Scheme 12. Asymmetric reductive arylation of aldehydes

图式13. 醛的不对称还原芳基化

Scheme 13. Asymmetric reductive arylation of aldehydes

图式14. 醛的不对称还原芳基化

Scheme 14. Asymmetric reductive arylation of aldehydes

图式15. 醛的不对称还原烯基化

Scheme 15. Asymmetric reductive alkenylation of aldehydes

图式16. 醛的不对称还原芳基化

Scheme 16. Asymmetric reductive arylation of aldehydes

图式17. α-酮酰胺的还原环化

Scheme 17. Reductive cyclization of α-ketoamides

图式18. 酮的不对称还原环化

Scheme 18. Asymmetric reductive cyclization of ketones

图式19. 酮的去对称化还原环化

Scheme 19. Desymmetrizative cyclization of ketones

图式20. 酮的不对称还原芳基化

Scheme 20. Asymmetric reductive arylation of ketones

图式21. 亚胺的还原烷基化

Scheme 21. Reductive alkylation of imines

图式22. 亚胺的不对称还原烷基化

Scheme 22. Asymmetric reductive alkylation of imines

图式23. 亚胺的不对称还原芳基化

Scheme 23. Asymmetric reductive arylation of imines

图式24. 醛的不对称还原芳基化

Scheme 24. Asymmetric reductive arylation of aldehydes

图式25. 芳基醛的还原芳基化

Scheme 25. Reductive arylation of aromatic aldehydes

图式26. 醛的不对称还原烯基化

Scheme 26. Asymmetric reductive alkenylation of aldehydes

图式27. 醛的不对称还原烯基化和芳基化

Scheme 27. Asymmetric reductive alkenylation and arylation of aldehydes

图式28. 醛的不对称还原芳基化

Scheme 28. Asymmetric reductive alkenylation and arylation of aldehydes

图式29. 醛的还原芳基化可能的机理

Scheme 29. Proposed mechanism for reductive arylation of aldehydes

图式30. 醛的还原芳基化

Scheme 30. Reductive arylation of aldehydes

图式31. 酮的不对称烷基芳基化

Scheme 31. Asymmetric reductive alkylation of ketones

图式32. 亚胺的还原芳基化

Scheme 32. Reductive arylation of imines

图式33. 亚胺的不对称还原芳基化

Scheme 33. Asymmetric reductive arylation of imines

图式34. 亚胺的不对称还原芳基化

Scheme 34. Asymmetric reductive alkenylation of imines

图式35. 亚胺的不对称还原烷基化

Scheme 35. Asymmetric reductive alkylation of imines

参考文献 51

[1]	(a) Chen, J.-Q.; Zhu, G.-G.; Wu, J. Acta Chim. Sinica 2024, 82, 190 (in Chinese).
	(陈健强, 朱钢国, 吴劼, 化学学报, 2024, 82, 190.)
	(b) Liu, Y.-H.; Gao, P. Acta Chim. Sinica 2024, 82, 1114 (in Chinese).
	(刘雨涵, 高盼, 化学学报, 2024, 82, 1114.)
	(c) Han, M.-L.; Xu, L.-H. Acta Chim. Sinica 2023, 81, 381 (in Chinese).
	(韩明亮, 徐丽华, 化学学报, 2023, 81, 381.)
	(d) Wang, X.-C.; Ji, Z.-Y.; Liu, J.; Wang, B.-F.; Jin, H.; Zhang, L.-X. Acta Chim. Sinica 2023, 81, 64 (in Chinese).
	(王晓晨, 季泽尧, 刘健, 王炳福, 金辉, 张立新, 化学学报, 2023, 81, 64.)
[2]	(a) Grignard, V. Compt. Rend. 1900, 130, 1322.
	(b) Collados, J. F.; Solà, R.; Harutyunyan, S. R.; Maciá, B. ACS Catal. 2016, 6, 1952.
	(c) Rong, J.-W.; Pellegrini, T.; Harutyunyan, S. R. Chem.-Eur. J. 2016, 22, 3558.
[3]	(a) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
	(b) Hatano, M.; Ishihara, K. Chem. Rec. 2008, 8, 143.
	(c) Pu, L. Acc. Chem. Res. 2014, 47, 1523.
[4]	Zong, H.; Huang, H.-Y.; Song, L. Tetrahedron: Asymmetry 2016, 27, 1069.
[5]	(a) Luo, R.-S.; Liao, J.-H.; Zhang, J. Chin. J. Org. Chem. 2013, 33, 2298 (in Chinese).
	(罗人仕, 廖建华, 张剑, 有机化学, 2013, 33, 2298.)
	(b) Quan, M.; Wu, L.; Yang, G.-Q.; Zhang, W.-B. Chem. Commun. 2018, 54, 10394.
	(c) Zhu, D.-X.; Xu, M.-H. Chin. J. Org. Chem. 2020, 40, 255 (in Chinese).
	(祝东星, 徐明华, 有机化学, 2020, 40, 255.)
[6]	Reformatsky, S. Ber. 1887, 20, 1210.
[7]	Barbier, P. C. R. Hebd. Séances Acad. Sci. 1899, 128, 110.
[8]	(a) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179.
	(b) McManus, H. A.; Cozzi, P. G.; Guiry, P. J. Adv. Synth. Catal. 2006, 348, 551.
	(c) Hargaden, G. C.; Guiry, P. J. Adv. Synth. Catal. 2007, 349, 2407.
	(d) Hargaden, G. C.; Guiry, P. J. Stereoselective Nozaki-Hiyama-Kishi Reaction. in Stereoselective Synthesis of Drugs and Natural Products, John Wiley & Sons, Ltd, 2013, pp. 1-22.
	(e) Tian, Q.-S.; Zhang, G.-Z. Synthesis 2016, 48, 4038.
	(f) Gil, A.; Albericio, F.; Álvarez, M. Chem. Rev. 2017, 117, 8420.
	(g) Katayama, Y.; Mitsunuma, H.; Kanai, M. Synthesis 2022, 54, 1684.
	(h) Kokić, B.; Vulović, B.; Jović, M.; Andrijević, A.; Ajdačić, V.; Opsenica, I. M. Eur. J. Org. Chem. 2023, 26, e202300997.
[9]	Majumdar, K. K.; Cheng, C.-H. Org. Lett. 2000, 2, 2295.
[10]	Huang, Y.-C.; Majumdar, K. K.; Cheng, C.-H. J. Org. Chem. 2002, 67, 1682.
[11]	Rayabarapu, D. K.; Chang, H.-T.; Cheng, C.-H. Chem.-Eur. J. 2004, 10, 2991.
[12]	Asachenko, A. F.; Valaeva, V. N.; Kudakina, V. A.; Uborsky, D. V.; Izmer, V. V.; Kononovich, D. S.; Voskoboynikov, A. Z. Russ. Chem. Bull. 2016, 65, 456.
[13]	Garcia, K. J.; Gilbert, M. M.; Weix, D. J. J. Am. Chem. Soc. 2019, 141, 1823.
[14]	Inaba, S.; Rieke, R. D. Tetrahedron Lett. 1985, 26, 155.
[15]	Durandetti, M.; Gosmini, C.; Périchon, J. Tetrahedron 2007, 63, 1146.
[16]	Ishida, S.; Suzuki, H.; Uchida, S.; Yamaguchi, E.; Itoh, A. Eur. J. Org. Chem. 2019, 2019, 7483.
[17]	Suzuki, H.; Yamaguchi, E.; Itoh, A. Synthesis 2021, 53, 1489.
[18]	Tan, Z.-Z.; Wan, X.-L.; Zang, Z.-H.; Qian, Q.; Deng, W.; Gong, H.-G. Chem. Commun. 2014, 50, 3827.
[19]	Cruz, C. L.; Montgomery, J. Chem. Sci. 2021, 12, 11995.
[20]	Yurino, T.; Ueda, Y.; Shimizu, Y.; Tanaka, S.; Nishiyama, H.; Tsurugi, H.; Sato, K.; Mashima, K. Angew. Chem., Int. Ed. 2015, 54, 14437.
[21]	Isbrandt, E. S.; Nasim, A.; Zhao, K.; Newman, S. G. J. Am. Chem. Soc. 2021, 143, 14646.
[22]	Nasim, A.; Thomas, G. T.; Ovens, J. S.; Newman, S. G. Org. Lett. 2022, 24, 7232.
[23]	Heitkämper, J.; Posada-Pérez, S.; Escayola, S.; Solà, M.; Kästner, J.; Poater, A. Chem.-Eur. J. 2023, 29, e202300193.
[24]	Liu, J.-J.; Chen, Y.-K.; Zhao, H.-P.; Yuan, W.-M. Org. Chem. Front. 2024, 11, 1205.
[25]	Hu, J.-X.; Wu, H.; Li, C.-Y.; Sheng, W.-J.; Jia, Y.-X.; Gao, J.-R. Chem.-Eur. J. 2011, 17, 5234.
[26]	He, J.-Q.; Chen, C.; Yu, W.-B.; Liu, R.-R.; Xu, M.; Li, Y.-J.; Gao, J.-R.; Jia, Y.-X. Tetrahedron Lett. 2014, 55, 2805.
[27]	Zhang, S.; Perveen, S.; Ouyang, Y.; Xu, L.; Yu, T.; Zhao, M.; Wang, L.-H.; Song, P.-D.; Li, P.-F. Angew. Chem., Int. Ed. 2022, 61, e202117843.
[28]	Zhu, Z.-Q.; Xiao, J.-S.; Li, M.-J.; Shi, Z.-Z. Angew. Chem., Int. Ed. 2022, 61, e202201370.
[29]	Gu, P.; Ding, L.-L.; Fang, X.-W.; Zhu, J.; Kang, S.-Y.; Wu, B.-C.; Zhang, J.; Zhao, Y.; Shi, Z.-Z. Angew. Chem., Int. Ed. 2024, 136, e202408195.
[30]	Jiang, M.-J.; Yu, L.-M.; Zou, C.-H.; Yuan, H.; Xu, M.-H.; Chen, B.; Hu, P.; Wang, B.-Q.; Cao, P. Chem.-Eur. J. 2024, 30, e202401591.
[31]	Tian, J.-Y.; Li, X.-N.; Shou, T.; Li, W.-D.; Lv, H. Chem.-Eur. J. 10.1002/chem.202403622.
[32]	Li, Y.; Li, W.-D.; Tian, J.-Y.; Huang, G.-Z.; Lv, H. Org. Lett. 2020, 22, 5353.
[33]	Zhou, P.; Xu, T. Chem. Commun. 2020, 56, 8194.
[34]	Huang, S.; Zhou, J. S. J. Am. Chem. Soc. 2024, 146, 12895.
[35]	(a) Turro, R. F.; Brandstätter, M.; Reisman, S. E. Angew. Chem., Int. Ed. 2022, 61, e202207597.
	(b) Oestreich, M.; Klare, H. F. T.; Brösamlen, D. Synfacts 2022, 18, 1098.
[36]	Zeng, W.-T.; Han, X.; Huang, G.-B.; Weng, J.; Chan, A. S. C.; Lu, G. Org. Chem. Front. 2023, 10, 1463.
[37]	Zhang, L.-Q.; Wang, X. -H.; Pu, M.-P.; Chen, C.-Y.; Yang, P.; Wu, Y.-D.; Chi, Y. R.; Zhou, J. S. J. Am. Chem. Soc. 2023, 145, 8498.
[38]	Chang, H.-T.; Jeganmohan, M.; Cheng, C.-H. Chem.-Eur. J. 2007, 13, 4356.
[39]	Presset, M.; Paul, J.; Cherif, G. N.; Ratnam, N.; Laloi, N.; Léonel, E.; Gosmini, C.; Gall, L. E. Chem.-Eur. J. 2019, 25, 4491.
[40]	Lin, C.-Y.; Zhang, J.-W.; Sun, Z.; Guo, Y.-L.; Chong, Q.-L.; Zhang, Z.-H.; Meng, F.-K. Angew. Chem., Int. Ed. 2024, 63, e202405290.
[41]	Chen, J.; Wu, L.-F.; Song, Z.-Y.; Wang, Y.; Li, Z.-K.; Wang, Y.; Zhu, S.-L. J. Am. Chem. Soc. 2024, 146, 26223.
[42]	(a) Jiang, X.; Jiang, H.; Yang, Q.; Cheng, Y.; Lu, L.-Q.; Tunge, J. A.; Xiao, W.-J. J. Am. Chem. Soc. 2022, 144, 8347.
	(b) Zhu, Z.-Q.; Shi, Z.-Z. Chin. J. Org. Chem. 2022, 42, 1872 (in Chinese).
	(朱子琦, 史壮志, 有机化学, 2022, 42, 1872.)
[43]	Jiang, H.; He, X.-K.; Jiang, X.; Zhao, W.; Lu, L.-Q.; Cheng, Y.; Xiao, W.-J. J. Am. Chem. Soc. 2023, 145, 6944.
[44]	Liang, T.-L.; Wu, Y.-T.; Sun, J.-Q.; Li, M.-R.; Zhao, H.-Q.; Zhang, J.-J.; Zheng, G.-F.; Zhang, Q. Chin. J. Chem. 2023, 41, 3253.
[45]	Han, T.-Y.; Mou, Q.-S.; Lv, Y.-Y.; Liu, M.-X. Green Chem. 2024, 26, 1370.
[46]	Xia, H.-Y.; Jiang, X.-N.; Lin, D.; Zhang, S.-P.; Yu, Z.-Y.; Wu, X.-Q.; Qu, J.-P.; Chen, Y.-F. J. Am. Chem. Soc. 2024, 146, 28468.
[47]	Presset, M.; Paul, J.; Cherif, G. N.; Ratnam, N.; Laloi, N.; Léonel, E.; Gosmini, C.; Le Gall, E. Chem.-Eur. J. 2019, 25, 4491.
[48]	(a) Xiao, J.-S.; Wang, M.-Y.; Yin, X.-W.; Yang, S.; Gu, P.; Lv, X.-L.; Zhao, Y.; Shi, Z.-Z. Angew. Chem., Int. Ed. 2023, 135, e202300743.
	(b) Xie, J.-Q.; Jia, Y.-X. Chin. J. Org. Chem. 2023, 43, 2256 (in Chinese).
	(谢佳琪, 贾义霞, 有机化学, 2023, 43, 2256.)
[49]	Xia, T.-T.; Wu, Y.-H.; Hu, J.-T.; Wu, X.-Q.; Qu, J.-P.; Chen, Y.-F. Angew. Chem., Int. Ed. 2024, 136, e202316012.
[50]	(a) Wu, X.-Q.; Xia, H.-Y.; Gao, C.-Y.; Luan, B.-X.; Wu, L.-C.; Zhang, C.-X.; Yang, D.-W.; Hou, L.-T.; Liu, N.; Xia, T.-T.; Li, H.-Y.; Qu, J.-P.; Chen, Y.-F. Nat. Chem. 2024, 16, 398.
	(b) Xia, T.-T.; Wu, W.-W.; Wu, X.-Q.; Qu, J.-P.; Chen, Y.-F. Angew. Chem., Int. Ed. 2024, 136, e202318991.
[51]	Zhang, C.-X.; Wu, X.-Q.; Qu, J.-P.; Chen, Y.-P. J. Am. Chem. Soc. 2024. 146, 25918.

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

RichHTML

PDF

可视化

摘要/Abstract

引用此文

分享此文

图/表 35

参考文献 51

相关文章 15

编辑推荐

相关统计

本文评价

[1]	杜一鸣, 贾均松, 李玉龙, 舒伟. 手性α-芳基酮的催化合成研究进展[J]. 有机化学, 2025, 45(6): 1838-1870.
[2]	张丛玉, 陈晓琦, 孟凡涛, 王海营, 郝文娟, 姜波. 金自接力催化1,3-烯炔醋酸酯与环醚缩醛的环化/亲核取代反应研究[J]. 有机化学, 2025, 45(6): 2199-2207.
[3]	马海宸, 周钧岍, 王嘉利, 王优, 朱少林. 镍催化的迁移偶联反应研究进展[J]. 有机化学, 2025, 45(6): 1871-1904.
[4]	谭永波, 舒洪波, 黄华文. 光诱导N-芳基丙烯酰胺参与的吲哚酮合成研究进展[J]. 有机化学, 2025, 45(6): 2086-2108.
[5]	陈刚, 陈东, 聂广杰, 李林轩, 姚辉, 王能中, 黄年玉. 有机膦催化下橙酮衍生的氮杂二烯与氨基巴豆酸酯的[2＋3]环加成反应[J]. 有机化学, 2025, 45(6): 2139-2148.
[6]	盛馨瑶, 李鑫鑫, 邢潇, 潘玲, 刘群, 李亦菲. 基于2-硝基查尔酮与异氰基乙酸乙酯的串联环化反应合成α-咔啉酮类化合物[J]. 有机化学, 2025, 45(6): 2163-2170.
[7]	蒋馨雨, 张新科, 方曦, 徐新芳. 蓝光诱导的α-硅氧基卡宾与1,3-二酮C—H键的形式上插入反应[J]. 有机化学, 2025, 45(6): 2231-2238.
[8]	谢沈彤, 李文静, 刘钰, 陆熹, 师仁义. 镍催化多氟芳烃与烷基卤化物的还原烷基化反应[J]. 有机化学, 2025, 45(6): 2121-2127.
[9]	高根伟, 李震, 李炎, 陆熹. 光/镍协同催化C(sp²)—C(sp³)键构建研究进展[J]. 有机化学, 2025, 45(6): 1905-1919.
[10]	车琳, 江忠涛, 杨慧, 胡芳东, 夏莹. 无过渡金属参与的偕二氟环丙烷双脱氟烷氧基化合成环丙酮缩酮[J]. 有机化学, 2025, 45(6): 2222-2230.
[11]	田曈, 陈镤, 黄华文. 可见光诱导芳香醛与苄烯丙二腈环化合成多取代二氢呋喃[J]. 有机化学, 2025, 45(5): 1763-1769.
[12]	刘俊杰, 赵红平, 胡媛媛, 汪恒昕, 袁伟明. 可见光诱导镍催化烯烃还原Heck反应[J]. 有机化学, 2025, 45(5): 1691-1697.
[13]	郭怡诗, 桑田, 刘岩, 刘平. 碱催化的β-酮腈与偶氮二甲酸酯的化学选择性取代反应[J]. 有机化学, 2025, 45(4): 1249-1260.
[14]	乔秀秀, 李倩, 赵世娜, 魏瑞琪, 马桃, 何永辉, 赵晓静. 2-取代的3H-吲哚-3-酮类化合物参与的C2位手性吲哚啉-3-酮类化合物的不对称合成研究进展[J]. 有机化学, 2025, 45(4): 1166-1177.
[15]	范玉兰, 邹小颖, 朱小青, 郑绿茵, 郭维. N-邻位C(sp³)—H键官能团化合成含氮杂环化合物研究进展[J]. 有机化学, 2025, 45(4): 1047-1096.