Visible-Light-Promoted Palladium-Catalyzed C—H Amination for the Synthesis of Carbazolequinones

doi:10.6023/cjoc202104037

Abstract

An intramolecular palladium-catalyzed cross-dehydrogenative C—H amination under blue LED irradiation at room temperature was developed. With oxygen as the external oxidant, a broad range of functional groups was compatible with the aromatic C—H amination of 2-amino-3-arylnaphthalene-1,4-diones, and diverse carbazolequinones can be obtained with good yields and excellent regioselectivity.

Key words: light-promoted, palladium-catalyzed, C—H amination, carbazolequinones

Cite this article

Yang Han, Weichao Jiang, Jing Zhang, Jinsong Peng, Chunxia Chen. Visible-Light-Promoted Palladium-Catalyzed C—H Amination for the Synthesis of Carbazolequinones[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 266-276.

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Entry	Pd	LEDs	Solvent	Yield^b/%
1	Pd(OAc)₂	—	DMSO	0
2	—	Blue (4 W)	DMSO	0
3^c	Pd(OAc)₂	Blue (4 W)	DMSO	74
4	Pd(OAc)₂	Blue (4 W)	NMP	11
5	Pd(OAc)₂	Blue (4 W)	Methanol	34
6	Pd(OAc)₂	Blue (4 W)	DCM	0
7	Pd(OAc)₂	Blue (4 W)	DCE	0
8	Pd(OAc)₂	Blue (4 W)	THF	0
9	Pd(OAc)₂	Blue (4 W)	1,4-Dioxane	0
10	Pd(OAc)₂	Blue (4 W)	DMF	0
11	Pd(OAc)₂	Blue (4 W)	Acetone	0
12	Pd(OAc)₂	Blue (4 W)	Toluene	0
13	PdCl₂	Blue (4 W)	DMSO	Trace
14	Pd(CF₃COO)₂	Blue (4 W)	DMSO	10
15	Pd₂(dba)₃	Blue (4 W)	DMSO	Trace
16	Pd(dppf)Cl₂	Blue (4 W)	DMSO	Trace
17	Pd(PPh₃)₄	Blue (4 W)	DMSO	Trace
18	Pd(PPh₃)₂Cl₂	Blue (4 W)	DMSO	Trace
19^c	Pd(OAc)₂	Blue (2 W)	DMSO	22
20^c	Pd(OAc)₂	Blue (6 W)	DMSO	21
21^c	Pd(OAc)₂	Blue (8 W)	DMSO	16
22^c	Pd(OAc)₂	Blue (10 W)	DMSO	36
23	Pd(OAc)₂	Purple (4 W)	DMSO	11
24	Pd(OAc)₂	Green (4 W)	DMSO	18

Entry	Pd	LEDs	Solvent	Yield^b/%
1	Pd(OAc)₂	—	DMSO	0
2	—	Blue (4 W)	DMSO	0
3^c	Pd(OAc)₂	Blue (4 W)	DMSO	74
4	Pd(OAc)₂	Blue (4 W)	NMP	11
5	Pd(OAc)₂	Blue (4 W)	Methanol	34
6	Pd(OAc)₂	Blue (4 W)	DCM	0
7	Pd(OAc)₂	Blue (4 W)	DCE	0
8	Pd(OAc)₂	Blue (4 W)	THF	0
9	Pd(OAc)₂	Blue (4 W)	1,4-Dioxane	0
10	Pd(OAc)₂	Blue (4 W)	DMF	0
11	Pd(OAc)₂	Blue (4 W)	Acetone	0
12	Pd(OAc)₂	Blue (4 W)	Toluene	0
13	PdCl₂	Blue (4 W)	DMSO	Trace
14	Pd(CF₃COO)₂	Blue (4 W)	DMSO	10
15	Pd₂(dba)₃	Blue (4 W)	DMSO	Trace
16	Pd(dppf)Cl₂	Blue (4 W)	DMSO	Trace
17	Pd(PPh₃)₄	Blue (4 W)	DMSO	Trace
18	Pd(PPh₃)₂Cl₂	Blue (4 W)	DMSO	Trace
19^c	Pd(OAc)₂	Blue (2 W)	DMSO	22
20^c	Pd(OAc)₂	Blue (6 W)	DMSO	21
21^c	Pd(OAc)₂	Blue (8 W)	DMSO	16
22^c	Pd(OAc)₂	Blue (10 W)	DMSO	36
23	Pd(OAc)₂	Purple (4 W)	DMSO	11
24	Pd(OAc)₂	Green (4 W)	DMSO	18

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