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

doi:10.6023/cjoc202206057

摘要/Abstract

报道了光催化N-氟代苯甲酰胺的1,5-氢原子转移和苄基自由基的偶联反应. 该反应表现出了良好的底物适用性和官能团兼容性, 以较好的产率得到了一系列重要的联苄基类化合物. 更重要的是, 该方法也适用于N-氟代的脂肪族酰胺.

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

引用此文

雷盼盼, 陈沁琳, 陈航, 周洋, 敬林海, 汪伟, 陈芬儿. 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[J]. 有机化学, 2023, 43(1): 254-264.

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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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