Rongalite Promoted Arylation of Benzoquinone

doi:10.19894/j.issn.1000-0518.220212

Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (3): 413-419.DOI: 10.19894/j.issn.1000-0518.220212

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Rongalite Promoted Arylation of Benzoquinone

Min-Xiao XU¹, Liang WANG²(), Cheng-Fang CHEN³

^1.Security Clearance Lab，Jiangsu Police Institute，Nanjing 210031，China
^2.School of Chemical and Pharmaceutical Engineering，Changzhou Vocational Institute of Engineering，Changzhou 213164，China
^3.Shandong Tian Bao Chemical Co. LTD，Pingyi 273300，China

Received:2022-06-14 Accepted:2022-11-10 Published:2023-03-01 Online:2023-03-27
Contact: Liang WANG
About author:lwcczu@126.com
Supported by:
China Postdoctoral Science Foundation(2018M632289);the “333” High-level Talents Training Project in Jiangsu Province of China

Abstract

Abstract:

The arylation reaction of benzoquinone using aryl iodides as the arylating reagent and rongalite （hydroxymethanesulfinic acid monosodium salt dihydrate） as the super electron donor has been developed under mild conditions. The reaction conditions are optimized using 4-iodonitrobenzene and benzoquinone as the model substrates. The effects of base， solvent， reaction temperature and substrate ratio on the reaction are investigated. Results show that the optimum reaction condition is as follows： 4-iodonitrobenzene （0.2 mmol）， benzoquinone （1 mmol）， rongalite （0.4 mmol）， potassium hydroxide （0.6 mmol）， DMSO （1 mL）， nitrogen atmosphere， 80 ℃ 24 h. Under this condition， the yield of the target product could reach up to 82%. Other aryl iodides and quinones also show good compatibilities， affording the corresponding products in 62%~84% yields.

Key words: Radical reaction, Arylation, Benzoquinone, Aryl iodides, Rongalite

CLC Number:

O621.3

Min-Xiao XU, Liang WANG, Cheng-Fang CHEN. Rongalite Promoted Arylation of Benzoquinone[J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 413-419.

Figures/Tables 5

References 18

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Entry	Product number	Isolated yield/%
1	3a	82
2	3b	62
3	3c	73
4	3d	75
5	3e	84
6	3f	72
7	3g	68
8	3h	71
9	3i	76
10	3j	70
11	3a	55（X=Br） 12（X=Cl）
12	3ka-3kc	71 （3∶5∶6=16∶50∶34）
13	3l	73

Entry	Product number	Isolated yield/%
1	3a	82
2	3b	62
3	3c	73
4	3d	75
5	3e	84
6	3f	72
7	3g	68
8	3h	71
9	3i	76
10	3j	70
11	3a	55（X=Br） 12（X=Cl）
12	3ka-3kc	71 （3∶5∶6=16∶50∶34）
13	3l	73

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Rongalite Promoted Arylation of Benzoquinone

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Figures/Tables 5

References 18

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Entry	Base	Solvent	Electron donor	Temperature/℃	Isolated yield/%
1	-	DMSO	Rongalite	80	<5
2	DBU	DMSO	Rongalite	80	18
3	K₂CO₃	DMSO	Rongalite	80	<5
4	K₃PO₄	DMSO	Rongalite	80	12
5	KOAc	DMSO	Rongalite	80	14
6	KOH	DMSO	Rongalite	80	67
7	NaOH	DMSO	Rongalite	80	51
8	KOH	DMF	Rongalite	80	11
9	KOH	CH₃CN	Rongalite	80	19
10	KOH	THF	Rongalite	80	0
11	KOH	1，4-Dioxane	Rongalite	80	0
12	KOH	MeOH	Rongalite	80	0
13	KOH	DMSO	-	80	0
14	KOH	DMSO	Na₂S₂O₄	80	25
15	KOH	DMSO	Rongalite	60	32
16	KOH	DMSO	Rongalite	100	61
17 ^b	KOH	DMSO	Rongalite	80	27
18 ^c	KOH	DMSO	Rongalite	80	55
19 ^d	KOH	DMSO	Rongalite	80	52
20 ^e	KOH	DMSO	Rongalite	80	82