Nickel/Visible Light Dual-Catalyzed C—O Bond Coupling Reactions of Aryl Bromides with Alcohols

doi:10.6023/cjoc202506009

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (1): 266-278.DOI: 10.6023/cjoc202506009 Previous Articles Next Articles

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镍/可见光协同催化的溴代芳烃与醇的C—O键偶联反应

高山^a^,^b^,^c, 解鑫^b^,^c^,^*(), 刘元红^a^,^b^,^c^,^*()

^a 郑州大学河南先进技术研究院郑州 450001
^b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
^c 中国科学院大学北京 100049

收稿日期:2025-06-05 修回日期:2025-07-24 发布日期:2025-08-26
通讯作者: 解鑫, 刘元红
基金资助:
中国科学院战略性先导科技专项(XDB0610000); 河南省科学院高层次人才科研启动基金(242002063)

Nickel/Visible Light Dual-Catalyzed C—O Bond Coupling Reactions of Aryl Bromides with Alcohols

Gao Shan^a^,^b^,^c, Xie Xin^b^,^c^,^*(), Liu Yuanhong^a^,^b^,^c^,^*()

^a Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001
^b State Key Laboratory of Organometallic Chemistry, Shanghai Inistitute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
^c University of Chinese Academy of Sciences, Beijing 100049

Received:2025-06-05 Revised:2025-07-24 Published:2025-08-26
Contact: Xie Xin, Liu Yuanhong
Supported by:
Strategic Priority Research Program of the Chinese Academy of Sciences(XDB0610000); High-Level Talent Research Start-Up Project Funding of Henan Academy of Sciences(242002063)

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Abstract

A nickel/visible light dual-catalyzed C—O bond coupling reaction between aryl/heteroaryl bromides and alcohols has been developed. Alkyl aryl ethers were efficiently synthesized by using organic photoredox-catalyst 2,4,5,6-tetra(9H-

carbazol-9-yl)isophthalonitrile (4CzIPN) or 2,4,5,6-tetrakis(diphenylamino)isophthalonitrile (4DPAIPN) in the presence of nickel(II) bromide 1,2-dimethoxyethane (NiBr₂•DME), a ligand, and a base under 456 nm blue LED irradiation at room temperature. The reaction likely involves the oxidative addition of Ni(0) intermediate to aryl bromide, ligand exchange with the alcohol, oxidization of the resulting Ni(II) intermediate by the excited photoredox catalyst to form Ni(III) intermediate, and subsequent reductive elimination. This method exhibits broad substrate scope of alcohols, including benzyl alcohols, primary alcohols, and secondary alcohols, and with remarkable functional group tolerance.

Key words: nickel-catalysis, visible light, C—O bond coupling, alkyl aryl ethers

Cite this article

Gao Shan, Xie Xin, Liu Yuanhong. Nickel/Visible Light Dual-Catalyzed C—O Bond Coupling Reactions of Aryl Bromides with Alcohols[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 266-278.

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Fig. & Tab. 6

References 34

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Entry	Photoredox-catalyst	Ni catalyst (mol%)	Ligand (mol%)	Base
1	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	^tBuOLi	59
2	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	Cs₂CO₃	5
3	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	MeOLi	65
4	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	88
5	4CzIPN	NiBr₂•DME (10)	L1 (10)	K₃PO₄	2
6	4CzIPN	NiBr₂•DME (10)	L2 (10)	K₃PO₄	68
7	4CzIPN	NiBr₂•DME (10)	L3 (10)	K₃PO₄	81
8	4CzIPN	NiCl₂•6H₂O (10)	dtbbpy (10)	K₃PO₄	79
9	[Ir(dFCF₃ppy)₂dtbbpy]PF₆	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	78
10	[Ir(dtbbpy)(ppy)₂]PF₆	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	50
11	4CzIPN	NiBr₂•DME (5)	dtbbpy (6)	K₃PO₄	88
12	4CzIPN	Ni(cod)₂(5)	dtbbpy (6)	K₃PO₄	84
13	—	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	1
14	4CzIPN	—	dtbbpy (10)	K₃PO₄	0
15	4CzIPN	NiBr₂•DME (10)	—	K₃PO₄	0
16	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	—	0
17^b	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	0
18^c	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	0

Entry	Photoredox-catalyst	Ni catalyst (mol%)	Ligand (mol%)	Base
1	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	^tBuOLi	59
2	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	Cs₂CO₃	5
3	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	MeOLi	65
4	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	88
5	4CzIPN	NiBr₂•DME (10)	L1 (10)	K₃PO₄	2
6	4CzIPN	NiBr₂•DME (10)	L2 (10)	K₃PO₄	68
7	4CzIPN	NiBr₂•DME (10)	L3 (10)	K₃PO₄	81
8	4CzIPN	NiCl₂•6H₂O (10)	dtbbpy (10)	K₃PO₄	79
9	[Ir(dFCF₃ppy)₂dtbbpy]PF₆	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	78
10	[Ir(dtbbpy)(ppy)₂]PF₆	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	50
11	4CzIPN	NiBr₂•DME (5)	dtbbpy (6)	K₃PO₄	88
12	4CzIPN	Ni(cod)₂(5)	dtbbpy (6)	K₃PO₄	84
13	—	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	1
14	4CzIPN	—	dtbbpy (10)	K₃PO₄	0
15	4CzIPN	NiBr₂•DME (10)	—	K₃PO₄	0
16	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	—	0
17^b	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	0
18^c	4CzIPN	NiBr₂•DME (10)	dtbbpy (10)	K₃PO₄	0

镍/可见光协同催化的溴代芳烃与醇的C—O键偶联反应

Nickel/Visible Light Dual-Catalyzed C—O Bond Coupling Reactions of Aryl Bromides with Alcohols

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