Oxidation of Sulfides with SO2F2/H2O2/Base

doi:10.6023/cjoc202111022

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1545-1550.DOI: 10.6023/cjoc202111022 Previous Articles Next Articles

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SO₂F₂/H₂O₂/碱和硫醚的氧化反应

周怡^a, 李卓骏^a, 胡明辉^b, 严兆华^a^,^*(), 林森^a^,^*()

a 南昌大学化学学院江西南昌 330031
b 浙江华海药业股份有限公司浙江临海 317024

收稿日期:2021-11-13 修回日期:2021-12-31 发布日期:2022-01-20
通讯作者: 严兆华, 林森
基金资助:
国家自然科学基金(21362022)

Oxidation of Sulfides with SO₂F₂/H₂O₂/Base

Yi Zhou^a, Zhuojun Li^a, Minghui Hu^b, Zhaohua Yan^a(), Sen Lin^a()

a College of Chemistry, Nanchang University, Nanchang, Jiangxi 330031
b Zhejiang Huahai Pharmaceutical Co., Ltd., Linhai, Zhejiang 317024

Received:2021-11-13 Revised:2021-12-31 Published:2022-01-20
Contact: Zhaohua Yan, Sen Lin
Supported by:
National Natural Science Foundation of China(21362022)

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Abstract

A novel oxidation system SO₂F₂/H₂O₂/base was investigated for the oxidation of sulfides and the corresponding sulfones were smoothly generated in good to excellent yields. The effects of base and solvent on oxidation were studied. The results showed that this oxidation system is tolerable to a variety of functional groups. A distinct advantage of this method is that by-products resulting from the use of the oxidation system are all water-soluble inorganic compounds, and can be conveniently removed after work-up process, therefore purification of the products is greatly simplified.

Key words: sulfuryl fluoride, hydrogen peroxide, oxidation, sulfides, sulfones

Cite this article

Yi Zhou, Zhuojun Li, Minghui Hu, Zhaohua Yan, Sen Lin. Oxidation of Sulfides with SO₂F₂/H₂O₂/Base[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1545-1550.

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References 13

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Entry	Base	Equivalent^b	Solvent	Yield/%^c
1	Et₃N	4	MeOH	50
2	DBU	4	MeOH	70
3	NaHCO₃	4	MeOH	52
4	NaOH	4	MeOH	75
5	K₂CO₃	1	MeOH	53
6	K₂CO₃	2	MeOH	79
7	K₂CO₃	3	MeOH	90
8	K₂CO₃	4	MeOH	93
9	K₂CO₃	5	MeOH	85
10	K₂CO₃	4	EtOH	87
11	K₂CO₃	4	CH₃COCH₃	27
12	K₂CO₃	4	i-PrOH	35
13	K₂CO₃	4	Et₂O	Trace
14	K₂CO₃	4	1,4-Dioxane	19
15	K₂CO₃	4	CH₂Cl₂	Trace
16	K₂CO₃	4	MeCN	39
17	K₂CO₃	4	DMSO	n.r.
18	K₂CO₃	4	PhMe	n.r.

Entry	Base	Equivalent^b	Solvent	Yield/%^c
1	Et₃N	4	MeOH	50
2	DBU	4	MeOH	70
3	NaHCO₃	4	MeOH	52
4	NaOH	4	MeOH	75
5	K₂CO₃	1	MeOH	53
6	K₂CO₃	2	MeOH	79
7	K₂CO₃	3	MeOH	90
8	K₂CO₃	4	MeOH	93
9	K₂CO₃	5	MeOH	85
10	K₂CO₃	4	EtOH	87
11	K₂CO₃	4	CH₃COCH₃	27
12	K₂CO₃	4	i-PrOH	35
13	K₂CO₃	4	Et₂O	Trace
14	K₂CO₃	4	1,4-Dioxane	19
15	K₂CO₃	4	CH₂Cl₂	Trace
16	K₂CO₃	4	MeCN	39
17	K₂CO₃	4	DMSO	n.r.
18	K₂CO₃	4	PhMe	n.r.

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SO₂F₂/H₂O₂/碱和硫醚的氧化反应

Oxidation of Sulfides with SO₂F₂/H₂O₂/Base

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SO2F2/H2O2/碱和硫醚的氧化反应