镍催化的迁移偶联反应研究进展

doi:10.6023/cjoc202408035

有机化学 ›› 2025, Vol. 45 ›› Issue (6): 1871-1904.DOI: 10.6023/cjoc202408035 上一篇下一篇

综述与进展

镍催化的迁移偶联反应研究进展

马海宸^a^,^†, 周钧岍^a^,^†, 王嘉利^a^,^†, 王优^a^,^*(), 朱少林^a^,^b^,^c^,^*()

^a 南京大学化学化工学院南京 210093
^b 河南师范大学化学化工学院河南新乡 453007
^c 上海交通大学上海市手性药物分子工程重点实验室上海 200240

收稿日期:2024-08-29 修回日期:2024-10-15 发布日期:2024-11-27
通讯作者: 王优, 朱少林
作者简介:
^†共同第一作者.
基金资助:
国家重点研发计划(2022YFA1503200); 国家自然科学基金(92156004); 国家自然科学基金(22271146); 国家自然科学基金(22271143); 江苏省国家科学基金(BK20230078); 河南师范大学化学与化学工程学院开放研究基金及上海市手性药物分子工程重点实验室开放研究基金资助项目

Recent Advances in Ni-Catalyzed Migratory Cross-Coupling Reactions

Haichen Ma^a^,^†, Junqian Zhou^a^,^†, Jiali Wang^a^,^†, You Wang^a^,^*(), Shaolin Zhu^a^,^b^,^c^,^*()

^a School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093
^b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
^c Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai 200240

Received:2024-08-29 Revised:2024-10-15 Published:2024-11-27
Contact: You Wang, Shaolin Zhu
About author:
^†The authors contributed equally to this work.
Supported by:
National Key R&D Program of China(2022YFA1503200); National Natural Science Foundation of China(92156004); National Natural Science Foundation of China(22271146); National Natural Science Foundation of China(22271143); Natural Science Foundation of Jiangsu Province(BK20230078); Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University, and the Open Research Fund of Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs

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摘要/Abstract

作为分子编辑的重要工具, 过渡金属催化的迁移偶联反应利用简单易得的原料, 结合金属动态迁移和选择性偶联来实现远程惰性C—H键的选择性官能团化, 从而简化合成路线, 提高合成效率. 近年来, 随着镍的迁移模式、多样性官能团化和选择性控制策略的发展, 镍催化的迁移偶联化学得到了快速的发展. 综述了镍催化的迁移偶联化学最新研究进展, 按照反应类型分为两部分: (1)迭代的1,2-金属迁移模式, 包括烯烃迁移单官能团化和烯烃迁移双官能团化(重点讨论迁移硼碳双官能团化), 实现远程C(sp³)—H键官能团化; (2)空间的1,4-金属迁移模式, 实现远程C(sp²)—H键官能团化.

关键词: 镍催化, 迁移偶联, 链行走, 1,4-Ni/H迁移, 烯烃, 配体接力催化

As a powerful tool for skeletal editing technology, transition-metal-catalyzed migratory cross-coupling enables the selective functionalization of distal C—H bonds through the synergistic combination of dynamic 1,n-M/H shift and selective cross-coupling utilizing readily accessible chemicals, thereby simplifying the synthesis route and improving synthesis efficiency. In the past decade, significant progress has been made in Ni-catalyzed migratory cross-coupling, including developments in modes of 1,n-Ni/H shift, diverse functionalization, and strategies to control the regio-and stereochemistry. The recent advancements in nickel-catalyzed migratory cross-coupling transformations are summarized, broadly categorized into two types: (1) migratory hydrofunctionalization and difunctionalization of olefins via iterative 1,2-Ni/H shift for the selective functionalization of remote C(sp³)—H bonds, and (2) migratory cross-coupling via through-space 1,4-Ni/H shift for the selective functionalization of remote C(sp²)—H bonds.

Key words: nickel catalysis, migratory cross-coupling, chain-walking, 1,4-Ni/H shift, alkene, ligand relay catalysis

引用此文

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.

Haichen Ma, Junqian Zhou, Jiali Wang, You Wang, Shaolin Zhu. Recent Advances in Ni-Catalyzed Migratory Cross-Coupling Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1871-1904.

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图/表 56

图式1. 镍催化的迁移偶联化学

Scheme 1. Ni-catalyzed migratory cross-coupling reactions

图式2. 镍氢催化烯烃的迁移还原氢芳基化

Scheme 2. NiH-Catalyzed reductive migratory hydroarylation of alkenes

图式3. 迁移氢芳基化合成α-芳基烷基硼酸酯

Scheme 3. Migratory hydroarylation to access α-aryl alkylboronates

图式4. 迁移不对称氢芳基化合成手性α-芳基烷基硼酸酯

Scheme 4. Asymmetric migratory hydroarylation to access chiral α-aryl alkylboronates

图式5. 迁移不对称氢芳基化合成手性1,1-二芳基烷烃

Scheme 5. Asymmetric migratory hydroarylation to access chiral 1,1-diarylalkanes

图式6. 远程含氮烯烃的迁移氢芳基化合成α-芳基脂肪胺

Scheme 6. Migratory hydroarylation of alkenyl amides to access α-aryl-substituted aliphatic amines

图式7. 迁移不对称氢芳基化合成手性α-芳基胺

Scheme 7. Asymmetric migratory hydroarylation to access chiral α-aryl-substituted amines

图式8. 使用烷基卤化物作为烯烃前体和氢源的迁移芳基化

Scheme 8. Migratory arylation using alkyl halide as olefin precursor and hydride source

图式9. 氧化还原中性条件下的迁移氢芳基化

Scheme 9. Migratory hydroarylation under redox-neutral conditions

图式10. 氧化还原中性条件下的迁移氢芳基化

Scheme 10. Migratory hydroarylation under redox-neutral conditions

图式11. 端位选择性的内烯烃迁移氢烷基化

Scheme 11. Migratory hydroalkylation of internal olefins with terminal regioselectivity

图式12. 内烯烃和α-杂原子取代的烷基卤的迁移氢烷基化

Scheme 12. Migratory hydroalkylation of internal olefins with α‑heteroatom substituted alkyl halides

图式13. 烯烃与消旋α-溴代酰胺的端位选择性迁移不对称氢烷基化

Scheme 13. Asymmetric migratory hydroalkylation of olefins and racemic α-bromo amides with terminal regioselectivity

图式14. α-氨基酰胺吡啶盐衍生物为烷基化试剂的迁移不对称氢烷基化

Scheme 14. Asymmetric migratory hydroalkylation using α-amino acids derived pyridinium salts as alkylation reagents

图式15. N-杂环烯烃迁移不对称氢烷基化

Scheme 15. Asymmetric migratory hydroalkylation of N-heterocyclic alkenes

图式16. 温度调控的区域发散性烯烃迁移氢烷基化

Scheme 16. Temperature regulated regiodivergent migratory hydroalkylation of alkenes

图式17. 配体调控的区域发散性烯烃迁移氢烷基化

Scheme 17. Ligand-controlled regiodivergent migratory hydroalkylation of alkenes

图式18. 远程醚导向的烯烃迁移不对称氢烷基化

Scheme 18. Ether-directed asymmetric migratory hydroalkylation

图式19. 固有酰胺导向的脱氨迁移氢烷基化

Scheme 19. Native amide-directed deaminative migratory hydroalkylation

图式20. 消旋环烯烃的迁移不对称氢烷基化

Scheme 20. Dynamic kinetic asymmetric migratory hydroalkylation of racemic cycloalkenes

图式21. 镍氢催化氮杂芳烃导向的烯烃迁移氢烷基化

Scheme 21. NiH-Catalyzed azaarene-directed migratory hydroalkylation

图式22. 配体控制烷基卤化物的区域多样性亲电交叉偶联

Scheme 22. Ligand-controlled regiodivergent migratory cross-electrophiles coupling of two alkyl halides

图式23. 烯烃与烯基亲电试剂的迁移氢烯基化

Scheme 23. Migratory hydroalkenylation of alkenes with alkenyl electrophiles

图式24. 烯烃与炔基溴化物的迁移氢炔基化

Scheme 24. Migratory hydroalkynylation of alkenes with alkynyl bromides

图式25. 镍氢催化的烯烃迁移脱氟交叉偶联

Scheme 25. NiH-catalyzed migratory defluorinative cross-coupling of olefin

图式26. 镍催化的卤代烷迁移远程C(sp3)—H羧基化

Scheme 26. Ni-catalyzed migratory carboxylation of discrete alkyl halides at remote C(sp3)—H sites

图式27. 镍催化的烯烃与CO2的迁移不对称氢羧基化反应

Scheme 27. Ni-catalyzed asymmetric migratory hydrocarboxylation of alkenes with CO2

图式28. 配体接力催化策略促进的卤代烷烯烃与烷基羧酸间的迁移还原不对称酰化

Scheme 28. Ligand relay catalysis enabled asymmetric reductive migratory acylation of alkyl halides with alkyl carboxylic acids

图式29. 配体接力催化策略促进的烯烃与烷基羧酸的迁移还原不对称氢酰化

Scheme 29. Ligand relay catalysis enabled asymmetric reductive migratory hydroacylation of alkenes with alkyl carboxylic acids

图式30. 镍催化的烯烃与硫醇的迁移氢硫化反应

Scheme 30. Ni-catalyzed migratory hydrothiolation of olefins with thiols

图式31. 镍催化的烯烃与硝基芳烃的迁移氢胺化反应

Scheme 31. Ni-catalyzed migratory hydroamination of olefins with nitroarenes

图式32. 配体调控的烯烃区域多样性迁移氢胺化

Scheme 32. Ligand-enabled regiodivergent migratory hydroamination

图式33. γ-位选择性迁移氢胺化

Scheme 33. γ-Selective migratory hydroamination

图式34. 硫醚导向的迁移氢胺化

Scheme 34. Thioether-directed migratory hydroamidation

图式35. 配体调控酰胺导向的区域多样性迁移氢胺化和迁移不对称氢胺化

Scheme 35. Ligand-controlled regiodivergent migratory hydroamination and enantioselective migratory hydroamination

图式36. 镍催化的烯烃与未活化胺和醇的直接迁移氢胺/醚化

Scheme 36. Ni-catalyzed migratory hydroamination and hydroetherification of alkenes with unactivated amines and alcohols

图式37. 镍催化的端烯烃迁移1,n-硼芳基化反应

Scheme 37. Ni-catalyzed migratory 1,n-arylboration of terminal alkenes

图式38. 镍催化的端烯烃迁移不对称1,1-硼芳基化反应

Scheme 38. Ni-catalyzed migratory asymmetric 1,1-arylboration of terminal alkenes

图式39. 镍催化环己烯和1,4-环己二烯的迁移1,3-硼芳基化

Scheme 39. Ni-catalyzed migratory 1,3-arylboration of cyclohexenes and 1,4-cyclohexadienes

图式40. 镍催化的端烯烃迁移1,1-硼苄基化反应

Scheme 40. Ni-catalyzed migratory 1,1-benzylboration of terminal alkenes

图式41. 镍催化的端烯烃迁移不对称1,1-硼烷基化反应

Scheme 41. Ni-catalyzed asymmetric migratory 1,1-alkylboration of terminal alkenes

图式42. 镍催化取代亚甲基环己烷的迁移1,1-硼苄基化反应

Scheme 42. Ni-catalyzed migratory 1,1-benzylboration of substituted methylenecyclohexanes

图式43. 镍催化的端烯烃迁移1,3-硼苄基化反应

Scheme 43. Ni-catalyzed migratory 1,3-benzylboration of terminal alkenes

图式44. 镍催化杂环烯烃迁移1,3-硼烷基化

Scheme 44. Ni-catalyzed migratory 1,3-alkylboration of endocyclic olefins

图式45. 镍催化环己烯和1,4-环己二烯的迁移1,3-硼烷基化

Scheme 45. Ni-catalyzed migratory 1,3-alkylboration of cyclohexenes and 1,4-cyclohexadienes

图式46. 镍催化的端烯烃迁移不对称1,1-硼烯基化反应

Scheme 46. Ni-catalyzed migratory asymmetric 1,1-alkenylboration of terminal alkenes

图式47. 镍催化的端烯烃迁移1,n-硼烯基化反应

Scheme 47. Ni-catalyzed migratory 1,n-alkenylboration of terminal alkenes

图式48. 镍催化的端烯烃迁移1,1-硼炔基化和1,1-双炔基化反应

Scheme 48. Ni-catalyzed migratory 1,1-alkynylboration and 1,1-dialkynylation of terminal alkenes

图式49. 镍催化的端烯烃迁移1,1-硼胺基化反应

Scheme 49. Ni-catalyzed migratory 1,1-aminoboration of terminal alkenes

图式50. 镍催化的烯烃迁移1,1-与1,3-硼胺基化反应

Scheme 50. Ni-catalyzed migratory 1,1-and 1,3-aminoboration of alkenes

图式51. 镍催化的苯炔异构化

Scheme 51. Ni-catalyzed isomerization of an aryne complex

图式52. 烯基到芳基1,4-镍/氢交换串联CO2偶联实现远程芳基C(sp2)—H羧基化

Scheme 52. Catalytic alkenyl-to-aryl 1,4-Ni/H shift followed by carboxylationcross-coupling with CO2 enabled aryl C(sp2)—H carboxylation

图式53. 烯基到芳基1,4-镍/氢交换过程实现芳基溴化物的原位/邻位双官能团化

Scheme 53. Catalytic alkenyl-to-aryl 1,4-Ni/H shift enabled ipso/ortho difunctionalization of aryl bromides

图式54. 烯基到芳基1,4-镍/氢交换过程

Scheme 54. Catalytic alkenyl-to-aryl 1,4-Ni/H shift enabled ipso/ortho alkenylation-hydroxylation of aryl bromides

图式55. 芳基碘化物的芳基到烯基1,4-镍迁移烷基化反应

Scheme 55. Migratory vinyl alkylation of aryl iodides via aryl-to-alkenyl 1,4-Ni/H shift

图式56. 芳基到烯基1,4-镍/氢迁移-还原偶联合成多取代烯烃

Scheme 56. Aryl-to-alkenyl 1,4-Ni/H shift/reductive coupling to access multisubstituted olefins

参考文献 63

[1]	Bullock, R. M.; Chen, J. G.; Gagliardi, L.; Chirik, P. J.; Farha, O. K.; Hendon, C. H.; Jones, C. W.; Keith, J. A.; Klosin, J.; Minteer, S. D.; Morris, R. H.; Radosevich, A. T.; Rauchfuss, T. B.; Strotman, N. A.; Vojvodic, A.; Ward, T. R.; Yang, J. Y.; Surendranath, Y. Science 2020, 369, No. eabc3183.
[2]	(a) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299.
	(b) Fu, G. C. ACS Cent. Sci. 2017, 3, 692.
	(c) Poremba, K. E.; Dibrell, S. E.; Reisman, S. E. ACS Catal. 2020, 10, 8237.
	(d) Diccianni, J. B.; Diao, T. Trends Chem. 2019, 1, 830.
	(e) Ogoshi, S. Nickel Catalysis in Organic Synthesis: Methods and Reactions, John Wiley & Sons, New York, 2019.
[3]	(a) Larionov, E.; Li, H.; Mazet, C. Chem. Commun. 2014, 50, 9816.
	(b) Vasseur, A.; Bruffaerts, J.; Marek, I. Nat. Chem. 2016, 8, 209.
	(c) Sommer, H.; Juliá-Hernández, F.; Martin, R.; Marek, I. ACS Cent. Sci. 2018, 4, 153.
	(d) Zhang, M.; Ji, Y.; Zhang, C. Chin. J. Chem. 2022, 40, 1608.
	(e) Wang, Y.; He, Y.; Zhu, S. Acc. Chem. Res. 2023, 56, 3475.
[4]	(a) Dhungana, R. K.; Sapkota, R. R.; Niroula, D.; Giri, R. Chem. Sci. 2020, 11, 9757.
	(b) Li, Y.; Yin, G. Acc. Chem. Res. 2023, 56, 3246.
[5]	(a) Shi, F.; Larock, R. C. Top. Curr. Chem. 2009, 292, 123.
	(b) Rahim, A.; Feng, J.; Gu, Z. Chin. J. Chem. 2019, 37, 929.
	(c) Li, M.-Y.; Wei, D.; Feng, C.-G.; Lin, G.-Q. T Chem.-Asian J. 2022, 17, e202200456.
[6]	(a) Möhring, V. M.; Fink, G. Angew. Chem., Int. Ed. 1985, 24, 1001.
	(b) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414.
[7]	He, Y.; Cai, Y.; Zhu, S. J. Am. Chem. Soc. 2017, 139, 1061.
[8]	Zhang, Y.; Han, B.; Zhu, S. Angew. Chem., Int. Ed. 2019, 58, 13860.
[9]	(a) Zhang, Y.; Ma, J.; Chen, J.; Meng, L.; Liang, Y.; Zhu, S. Chem 2021, 7, 3171.
	(b) He, Y.; Ma, J.; Song, H.; Zhang, Y.; Liang, Y.; Wang, Y.; Zhu, S. Nat. Commun. 2022, 13, 2471.
[10]	Shi, H.; Wang, J.; Zhu, Y.; Li, H.; Ju, G.; Zhang, L.; Wang, C. Chin. Chem. Lett. 2024, 35, 109333.
[11]	Zhou, J.; He, Y.; Liu, Z.; Wang, Y.; Zhu, S. Adv. Sci. 2024, 11, 2306447.
[12]	Chen, F.; Chen, K.; Zhang, Y.; He, Y.; Wang, Y.-M.; Zhu, S. J. Am. Chem. Soc. 2017, 139, 13929.
[13]	(a) Li, Y.; Luo, Y.; Peng, L.; Li, Y.; Zhao, B.; Wang, W.; Pang, H.; Deng, Y.; Bai, R.; Lan, Y.; Yin, G. Nat. Commun. 2020, 11, 417.
	(b) He, H.-D.; Chitrakar, R.; Cao, Z.-W.; Wang, D.-M.; She, L.-Q.; Zhao, P.-G.; Wu, Y.; Xu, Y.-Q.; Cao, Z.-Y.; Wang, P. Angew. Chem., Int. Ed. 2024, 63, e202313336.
[14]	He, Y.; Liu, C.; Yu, L.; Zhu, S. Angew. Chem., Int. Ed. 2020, 59, 9186.
[15]	Zhou, F.; Zhu, J.; Zhang, Y.; Zhu, S. Angew. Chem., Int. Ed. 2018, 57, 4058.
[16]	(a) Sun, S.-Z.; Börjesson, M.; Martin-Montero, R.; Martin, R. J. Am. Chem. Soc. 2018, 140, 12765.
	(b) Yue, W.-J.; Martin, R. ACS Catal. 2022, 12, 12132.
[17]	Zhou, F.; Zhang, Y.; Xu, X.; Zhu, S. Angew. Chem., Int. Ed. 2019, 58, 1754.
[18]	Wang, Z.; Yin, H.; Fu, G. C. Nature 2018, 563, 379.
[19]	Sun, S.-Z.; Cai, Y.-M.; Zhang, D.-L.; Wang, J.-B.; Yao, H.-Q.; Rui, X.-Y.; Martin, R.; Shang, M. J. Am. Chem. Soc. 2022, 144, 1130.
[20]	Qian, D.; Hu, X. Angew. Chem., Int. Ed. 2019, 58, 18519.
[21]	Wang, X.; Xue, J.; Rong, Z.-Q. J. Am. Chem. Soc. 2023, 145, 15456.
[22]	Chen, C.; Guo, W.; Qiao, D.; Zhou, J.; Wang, Y.; Zhu, S. CCS Chem. 2023, 6, 898.
[23]	Wang, J.-W.; Liu, D.-G.; Chang, Z.; Li, Z.; Fu, Y.; Lu, X. Angew. Chem., Int. Ed. 2022, 61, e202205537.
[24]	Yang, P.-F.; Shu, W. Angew. Chem., Int. Ed. 2022, 61, e202208018.
[25]	Zhao, L.; Zhu, Y.; Liu, M.; Xie, L.; Liang, J.; Shi, H.; Meng, X.; Chen, Z.; Han, J.; Wang, C. Angew. Chem., Int. Ed. 2022, 61, e202204716.
[26]	Wang, J.-W.; Li, Z.; Liu, D.; Zhang, J.-Y.; Lu, X.; Fu, Y. J. Am. Chem. Soc. 2023, 145, 10411.
[27]	Rodrigalvarez, J.; Wang, H.; Martin, R. J. Am. Chem. Soc. 2023, 145, 3869.
[28]	Chen, C.; Guo, W.; Qiao, D.; Zhu, S. Angew. Chem., Int. Ed. 2023, 62, e202308320.
[29]	Shao, Y.-P.; Chi, Z.-M.; Liang, Y.-M. Sci. China: Chem. 2024, 67, 1935.
[30]	Zhao, W.-T.; Meng, H.; Lin, J.-N.; Shu, W. Angew. Chem., Int. Ed. 2023, 62, e202215779.
[31]	(a) Liu, J.; Gong, H.; Zhu, S. Angew. Chem., Int. Ed. 2021, 60, 4060.
	(b) Zhang, P.; Zhang, M.; Ji, Y.; Xing, M.; Zhao, Q.; Zhang, C. Org. Lett. 2020, 22, 8285.
[32]	(a) Jiang, X.; Han, B.; Xue, Y.; Duan, M.; Gui, Z.; Wang, Y.; Zhu, S. Nat. Commun. 2021, 12, 3792.
	(b) Liu, M.; Shi, H.; Meng, X.; He, R.; Huang, J.; Wang, J.; Lv, J.; Wang, C. CCS Chem. 2023, 6, 1929.
[33]	(a) Chen, F.; Xu, X.; He, Y.; Huang, G.; Zhu, S. Angew. Chem., Int. Ed. 2020, 59, 5398.
	(b) Zhu, L.; Huang, J.; Meng, F.; Tan, Z.; Meng, X.; Xiao, Y.; Zhang, L.; Li, W.; Wang, C. Org. Chem. Front. 2023, 10, 5623.
[34]	Juliá-Hernández, F.; Moragas, T.; Cornella, J.; Martin, R. Nature 2017, 545, 84.
[35]	Zhou, L.; Li, L.; Zhang, S.; Kuang, X.-K.; Zhou, Y.-Y.; Tang, Y. J. Am. Chem. Soc. 2024, 146, 18823.
[36]	He, J.; Song, P.; Xu, X.; Zhu, S.; Wang, Y. ACS Catal. 2019, 9, 3253.
[37]	Jiang, X.; Sheng, F.-T.; Zhang, Y.; Deng, G.; Zhu, S. J. Am. Chem. Soc. 2022, 144, 21448.
[38]	Zhang, Y.; Xu, X.; Zhu, S. Nat. Commun. 2019, 10, 1752.
[39]	Xiao, J.; He, Y.; Ye, F.; Zhu, S. Chem 2018, 4, 1645.
[40]	Zhang, Y.; He, J.; Song, P.; Wang, Y.; Zhu, S. CCS Chem. 2020, 3, 2259.
[41]	Lee, C.; Seo, H.; Jeon, J.; Hong, S. Nat. Commun. 2021, 12, 5657.
[42]	Du, B.; Ouyang, Y.; Chen, Q.; Yu, W.-Y. J. Am. Chem. Soc. 2021, 143, 14962.
[43]	Xie, L.; Liang, J.; Bai, H.; Liu, X.; Meng, X.; Xu, Y.-Q.; Cao, Z.-Y.; Wang, C. ACS Catal. 2023, 13, 10041.
[44]	Song, T.; Luo, Y.; Wang, K.; Wang, B.; Yuan, Q.; Zhang, W. ACS Catal. 2023, 13, 4409.
[45]	Wang, W.; Ding, C.; Li, Y.; Li, Z.; Li, Y.; Peng, L.; Yin, G. Angew. Chem., Int. Ed. 2019, 58, 4612.
[46]	Wang, W.; Ding, C.; Yin, G. Nat. Catal. 2020, 3, 951.
[47]	(a) Kong, W.; Bao, Y.; Lu, L.; Han, Z.; Zhong, Y.; Zhang, R.; Li, Y.; Yin, G. Angew. Chem., Int. Ed. 2023, 62, e202308041.
	(b) Ren, Y.; Wang, L.; Ding, C.; Li, Y.; Yin, G. Chin. J. Chem. 2024, 42, 356.
[48]	Li, Y.; Pang, H.; Wu, D.; Li, Z.; Wang, W.; Wei, H.; Fu, Y.; Yin, G. Angew. Chem., Int. Ed. 2019, 58, 8872.
[49]	Li, Z.; Shi, H.; Chen, X.; Peng, L.; Li, Y.; Yin, G. J. Am. Chem. Soc. 2023, 145, 13603.
[50]	Li, Y.; Li, Y.; Shi, H.; Wei, H.; Li, H.; Funes-Ardoiz, I.; Yin, G. Science 2022, 376, 749.
[51]	Li, Y.; Wei, H.; Yin, G. Tetrahedron Lett. 2022, 100, 153889.
[52]	Ding, C.; Ren, Y.; Sun, C.; Long, J.; Yin, G. J. Am. Chem. Soc. 2021, 143, 20027.
[53]	Sun, C.; Li, Y.; Yin, G. Angew. Chem., Int. Ed. 2022, 61, e202209076.
[54]	Sun, C.; Ding, C.; Yu, Y.; Li, Y.; Yin, G. Fundam. Res. https://doi.org/10.1016/j.fmre.2023.03.016.
[55]	Li, Y.; Wei, H.; Wu, D.; Li, Z.; Wang, W.; Yin, G. ACS Catal. 2020, 10, 4888.
[56]	Talavera, L.; Freund, R. R. A.; Zhang, H.; Wakeling, M.; Jensen, M.; Martin, R. ACS Catal. 2023, 13, 5538.
[57]	Lyu, M.-Y.; Morais, G. N.; Chen, S.; Brown, M. K. J. Am. Chem. Soc. 2023, 145, 27254.
[58]	Keen, A. L.; Johnson, S. A. J. Am. Chem. Soc. 2006, 128, 1806.
[59]	Börjesson, M.; Janssen-Müller, D.; Sahoo, B.; Duan, Y.; Wang, X.; Martin, R. J. Am. Chem. Soc. 2020, 142, 16234.
[60]	He, Y.; Börjesson, M.; Song, H.; Xue, Y.; Zeng, D.; Martin, R.; Zhu, S. J. Am. Chem. Soc. 2021, 143, 20064.
[61]	Zhang, H.; Rodrigalvarez, J.; Martin, R. J. Am. Chem. Soc. 2023, 145, 17564.
[62]	Wang, C.-T.; Liang, P.-Y.; Li, M.; Wang, B.; Wang, Y.-Z.; Li, X.-S.; Wei, W.-X.; Gou, X.-Y.; Ding, Y.-N.; Zhang, Z.; Li, T.-K.; Liu, X.-Y.; Liang, Y.-M. Angew. Chem., Int. Ed. 2023, 62, e202304447.
[63]	Yang, J.; Gui, Z.; He, Y.; Zhu, S. Angew. Chem., Int. Ed. 2023, 62, e202304713.

镍催化的迁移偶联反应研究进展

Recent Advances in Ni-Catalyzed Migratory Cross-Coupling Reactions

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