Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides

doi:10.6023/cjoc202303004

Abstract

In this study, a visible-light photoredox-catalyzed difluoroalkylation of newly designed functionalized aromatic isocyanides with commercially available CF₂ precursors was reported. A series of CF₂-containing indole-1,2-fused diazepanones were constructed in cascade reaction through a sequence of radical addition/cyclization processes under mild conditions. This reaction not only generated a class of polycyclic indole fused seven-membered nitrogen heterocycles but also expanded the reactions of functionalized isocyanides.

Key words: functionalized aromatic isocyanides, radical cyclization, difluoroalkylation, indole fused seven-membered nitrogen heterocycles

Cite this article

Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.

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Entry	Catalyst	Base	Solvent	Yield^b/%
1	fac-Ir(ppy)₃	Na₂HPO₄	DMF	51
2	fac-Ir(ppy)₃	NaHCO₃	DMF	62
3	fac-Ir(ppy)₃	KHCO₃	DMF	42
4	fac-Ir(ppy)₃	Na₂CO₃	DMF	32
5	fac-Ir(ppy)₃	Cs₂CO₃	DMF	26
6	fac-Ir(ppy)₃	Et₃N	DMF	27
7	fac-Ir(ppy)₃	2,6-Lutidine	DMF	53
8	fac-Ir(ppy)₃	DBU	DMF	7
9	fac-Ir(ppy)₃	NaHCO₃	DCM	19
10	fac-Ir(ppy)₃	NaHCO₃	CH₃CN	14
11	fac-Ir(ppy)₃	NaHCO₃	DMAc	47
12	fac-Ir(ppy)₃	NaHCO₃	DMSO	27
13	fac-Ir(ppy)₃	NaHCO₃	THF	45
14	fac-Ir(ppy)₃	NaHCO₃	Toluene	42
15	Ru(bpy)₃Cl₂•6H₂O	NaHCO₃	DMF	8
16	4CzIPN	NaHCO₃	DMF	22
17	Eosin Y	NaHCO₃	DMF	Trace
18	Methylene Blue	NaHCO₃	DMF	10
19	fac-Ir(ppy)₃	—	DMF	24
20	—	NaHCO₃	DMF	8
21^c	fac-Ir(ppy)₃	NaHCO₃	DMF	0
22^d	fac-Ir(ppy)₃	NaHCO₃	DMF	50
23^e	fac-Ir(ppy)₃	NaHCO₃	DMF	43

Entry	Catalyst	Base	Solvent	Yield^b/%
1	fac-Ir(ppy)₃	Na₂HPO₄	DMF	51
2	fac-Ir(ppy)₃	NaHCO₃	DMF	62
3	fac-Ir(ppy)₃	KHCO₃	DMF	42
4	fac-Ir(ppy)₃	Na₂CO₃	DMF	32
5	fac-Ir(ppy)₃	Cs₂CO₃	DMF	26
6	fac-Ir(ppy)₃	Et₃N	DMF	27
7	fac-Ir(ppy)₃	2,6-Lutidine	DMF	53
8	fac-Ir(ppy)₃	DBU	DMF	7
9	fac-Ir(ppy)₃	NaHCO₃	DCM	19
10	fac-Ir(ppy)₃	NaHCO₃	CH₃CN	14
11	fac-Ir(ppy)₃	NaHCO₃	DMAc	47
12	fac-Ir(ppy)₃	NaHCO₃	DMSO	27
13	fac-Ir(ppy)₃	NaHCO₃	THF	45
14	fac-Ir(ppy)₃	NaHCO₃	Toluene	42
15	Ru(bpy)₃Cl₂•6H₂O	NaHCO₃	DMF	8
16	4CzIPN	NaHCO₃	DMF	22
17	Eosin Y	NaHCO₃	DMF	Trace
18	Methylene Blue	NaHCO₃	DMF	10
19	fac-Ir(ppy)₃	—	DMF	24
20	—	NaHCO₃	DMF	8
21^c	fac-Ir(ppy)₃	NaHCO₃	DMF	0
22^d	fac-Ir(ppy)₃	NaHCO₃	DMF	50
23^e	fac-Ir(ppy)₃	NaHCO₃	DMF	43

可见光诱导的新型官能化芳基异腈化合物的二氟烷基化环化反应