Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides

doi:10.6023/cjoc202206057

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 254-264.DOI: 10.6023/cjoc202206057 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

ARTICLES

可见光促进N-氟代酰胺的1,5-氢迁移和自由基偶联反应合成联苄基衍生物

雷盼盼^a, 陈沁琳^a, 陈航^a, 周洋^a, 敬林海^a^,^*(), 汪伟^a^,^b^,^*(), 陈芬儿^b^,^c^,^*()

a 西华师范大学化学化工学院四川南充 637002
b 武汉工程大学药物研究院武汉 430205
c 复旦大学化学学院上海 200433

收稿日期:2022-06-30 修回日期:2022-07-30 发布日期:2022-08-25
通讯作者: 敬林海, 汪伟, 陈芬儿
基金资助:
国家自然科学基金(21602144); 四川省科技计划(2021ZYD0064); 及湖北省教育厅科研计划(Q20211503)

Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides

Panpan Lei^a, Qinlin Chen^a, Hang Chen^a, Yang Zhou^a, Linhai Jin^a(), Wei Wang^a^,^b(), Fener Chen^b^,^c()

a College of Chemistry and Chemical Engineering, China West Normal University, Nanchong, Sichuan 637002
b Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205
c Department of Chemistry, Fudan University, Shanghai 200433

Received:2022-06-30 Revised:2022-07-30 Published:2022-08-25
Contact: Linhai Jin, Wei Wang, Fener Chen
Supported by:
National Natural Science Foundation of China(21602144); Science and Technology Program of Sichuan Province(2021ZYD0064); Scientific Research Project of Education Department of Hubei Province(Q20211503)

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Abstract

Visible light-mediated 1,5-hydrogen atom transfer and radical coupling reactions have been accomplished using N-fluoro-substituted benzamides. This method exhibits a broad substrate scope and high functional group tolerance, giving the corresponding bibenzyl products with generally good yields. Furthermore, this strategy could also be used to N-fluoro-substi- tuted aliphatic amides.

Key words: bibenzyl derivative, 1,5-hydrogen atom transfer, radical coupling, visible-light

Cite this article

Panpan Lei, Qinlin Chen, Hang Chen, Yang Zhou, Linhai Jin, Wei Wang, Fener Chen. Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 254-264.

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Fig. & Tab. 7

References 22

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Entry	Photocatalyst	λ/nm	Base	Solvent	Yield^b/%
1	fac-Ir(ppy)₃	420	Et₃N	CH₃CN	50
2	fac-Ir(ppy)₃	420	Et₃N	DCM	55
3	fac-Ir(ppy)₃	420	Et₃N	DMF	30
4	fac-Ir(ppy)₃	420	Et₃N	DMSO	32
5	fac-Ir(ppy)₃	420	Et₃N	THF	60
6	fac-Ir(ppy)₃	420	Et₃N	2-MeTHF	95
7	fac-Ir(ppy)₃	420	DBU	2-MeTHF	30
8	fac-Ir(ppy)₃	420	K₂CO₃	2-MeTHF	35
9	fac-Ir(ppy)₃	420	K₃PO₄	2-MeTHF	50
10	fac-Ir(ppy)₃	420	NaO^tBu	2-MeTHF	22
11	fac-Ir(ppy)₃	420	—	2-MeTHF	38
12	fac-Ir(p-Fppy)₃	420	Et₃N	2-MeTHF	45
13	[Ir(dFCF₃ppy)₂(bpy)]PF₆	420	Et₃N	2-MeTHF	65
14	Ru(phen)₃(PF₆)₂	420	Et₃N	2-MeTHF	57
15	4-CzIPN	420	Et₃N	2-MeTHF	0
16	Eosin Y	420	Et₃N	2-MeTHF	10
17	fac-Ir(ppy)₃	400	Et₃N	2-MeTHF	70
18	fac-Ir(ppy)₃	365	Et₃N	2-MeTHF	90
19^c	fac-Ir(ppy)₃	—	Et₃N	2-MeTHF	0

Entry	Photocatalyst	λ/nm	Base	Solvent	Yield^b/%
1	fac-Ir(ppy)₃	420	Et₃N	CH₃CN	50
2	fac-Ir(ppy)₃	420	Et₃N	DCM	55
3	fac-Ir(ppy)₃	420	Et₃N	DMF	30
4	fac-Ir(ppy)₃	420	Et₃N	DMSO	32
5	fac-Ir(ppy)₃	420	Et₃N	THF	60
6	fac-Ir(ppy)₃	420	Et₃N	2-MeTHF	95
7	fac-Ir(ppy)₃	420	DBU	2-MeTHF	30
8	fac-Ir(ppy)₃	420	K₂CO₃	2-MeTHF	35
9	fac-Ir(ppy)₃	420	K₃PO₄	2-MeTHF	50
10	fac-Ir(ppy)₃	420	NaO^tBu	2-MeTHF	22
11	fac-Ir(ppy)₃	420	—	2-MeTHF	38
12	fac-Ir(p-Fppy)₃	420	Et₃N	2-MeTHF	45
13	[Ir(dFCF₃ppy)₂(bpy)]PF₆	420	Et₃N	2-MeTHF	65
14	Ru(phen)₃(PF₆)₂	420	Et₃N	2-MeTHF	57
15	4-CzIPN	420	Et₃N	2-MeTHF	0
16	Eosin Y	420	Et₃N	2-MeTHF	10
17	fac-Ir(ppy)₃	400	Et₃N	2-MeTHF	70
18	fac-Ir(ppy)₃	365	Et₃N	2-MeTHF	90
19^c	fac-Ir(ppy)₃	—	Et₃N	2-MeTHF	0

可见光促进N-氟代酰胺的1,5-氢迁移和自由基偶联反应合成联苄基衍生物

Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides

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