Recent Advances in Ni-Catalyzed Migratory Cross-Coupling Reactions

doi:10.6023/cjoc202408035

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 1871-1904.DOI: 10.6023/cjoc202408035 Previous Articles Next Articles

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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

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

Cite this article

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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Fig. & Tab. 56

Scheme 1. Ni-catalyzed migratory cross-coupling reactions

Scheme 2. NiH-Catalyzed reductive migratory hydroarylation of alkenes

Scheme 3. Migratory hydroarylation to access α-aryl alkylboronates

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

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

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

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

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

Scheme 9. Migratory hydroarylation under redox-neutral conditions

Scheme 10. Migratory hydroarylation under redox-neutral conditions

Scheme 11. Migratory hydroalkylation of internal olefins with terminal regioselectivity

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

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

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

Scheme 15. Asymmetric migratory hydroalkylation of N-heterocyclic alkenes

Scheme 16. Temperature regulated regiodivergent migratory hydroalkylation of alkenes

Scheme 17. Ligand-controlled regiodivergent migratory hydroalkylation of alkenes

Scheme 18. Ether-directed asymmetric migratory hydroalkylation

Scheme 19. Native amide-directed deaminative migratory hydroalkylation

Scheme 20. Dynamic kinetic asymmetric migratory hydroalkylation of racemic cycloalkenes

Scheme 21. NiH-Catalyzed azaarene-directed migratory hydroalkylation

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

Scheme 23. Migratory hydroalkenylation of alkenes with alkenyl electrophiles

Scheme 24. Migratory hydroalkynylation of alkenes with alkynyl bromides

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

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

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

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

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

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

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

Scheme 32. Ligand-enabled regiodivergent migratory hydroamination

Scheme 33. γ-Selective migratory hydroamination

Scheme 34. Thioether-directed migratory hydroamidation

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 51. Ni-catalyzed isomerization of an aryne complex

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

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

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

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

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

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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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