Synthesis of β-Ketosulfone from Sodium Sulfinate and Aryl Ethyl Ketone/Indanone

doi:10.6023/cjoc202109050

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4749-4757.DOI: 10.6023/cjoc202109050 Previous Articles Next Articles

Special Issue: 绿色合成化学专辑；热点论文虚拟合集

ARTICLES

亚磺酸钠盐和芳基乙酮/茚酮合成β-酮砜

刘丽^a, 肖洪^a, 肖福红^a^,^b^,^*(), 谢艳军^b, 黄华文^a^,^*(), 邓国军^a

a 湘潭大学绿色有机合成与应用湖南省重点实验室湖南湘潭 411105
b 湖南工程学院环境催化与废弃物再生化湖南省重点实验室湖南湘潭 411104

收稿日期:2021-09-30 修回日期:2021-11-05 发布日期:2021-11-09
通讯作者: 肖福红, 黄华文
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21871226); 国家自然科学基金(21502160); 国家自然科学基金(21572194); 湖南省教育厅优秀青年(19B564)

Synthesis of β-Ketosulfone from Sodium Sulfinate and Aryl Ethyl Ketone/Indanone

Li Liu^a, Hong Xiao^a, Fuhong Xiao^a^,^b(), Yanjun Xie^b, Huawen Huang^a(), Guojun Deng^a

a Hunan Key Laboratory of Green Organic Synthesis and Application, Xiangtan University, Xiangtan, Hunan 411105
b Hunan Key Laboratory of Environmental Catalysis and Waste Rebiochemistry, Hunan Institute of Engineering, Xiangtan, Hunan 411104

Received:2021-09-30 Revised:2021-11-05 Published:2021-11-09
Contact: Fuhong Xiao, Huawen Huang
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21871226); National Natural Science Foundation of China(21502160); National Natural Science Foundation of China(21572194); Scientific Research Fund of Hunan Provincial Education Department(19B564)

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Abstract

An efficient and convenient strategy for the preparation of β-ketosulfone via C—H bond functionalization with sodium sulfite and aryl ethyl ketone/indenone under metal-free condition has been reported. The method has simple operation steps, mild reaction conditions and good functional group compatibility. The reaction enables the direct formation of C(sp³)—H into C—S bonds, thereby avoiding the use of strong oxidants and prefunctionalization of substrates. The β-ketosulfone compounds can be transformed as intermediates in organic synthesis.

Key words: sodium sulfintes, β-keto sulfones, C—H functionalization, C—S bond, transition metal-free

Cite this article

Li Liu, Hong Xiao, Fuhong Xiao, Yanjun Xie, Huawen Huang, Guojun Deng. Synthesis of β-Ketosulfone from Sodium Sulfinate and Aryl Ethyl Ketone/Indanone[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4749-4757.

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References 25

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Entry	Addtive (equiv.)	Solvent	Yield^b/%
1	TBAI (2.0)	DMSO/AcOH (V∶V=1∶1)	47
2	NH₄I (2.0)	DMSO/AcOH (V∶V=1∶1)	Trace
3	NaI (2.0)	DMSO/AcOH (V∶V=1∶1)	50
4	I₂ (1.0)	DMSO/AcOH (V∶V=1∶1)	Trace
5	KI (2.0)	DMSO/AcOH (V∶V=1∶1)	53
6	KI (1.0)	DMSO/AcOH (V∶V=1∶1)	53
7	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	57
8	KI (1.5)	DMSO/AcOH (V∶V=1∶3)	35
9	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	33
10^c	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	51
11^d	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	43
12^e	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	50
13^f	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	34
14^g	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	34

Entry	Addtive (equiv.)	Solvent	Yield^b/%
1	TBAI (2.0)	DMSO/AcOH (V∶V=1∶1)	47
2	NH₄I (2.0)	DMSO/AcOH (V∶V=1∶1)	Trace
3	NaI (2.0)	DMSO/AcOH (V∶V=1∶1)	50
4	I₂ (1.0)	DMSO/AcOH (V∶V=1∶1)	Trace
5	KI (2.0)	DMSO/AcOH (V∶V=1∶1)	53
6	KI (1.0)	DMSO/AcOH (V∶V=1∶1)	53
7	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	57
8	KI (1.5)	DMSO/AcOH (V∶V=1∶3)	35
9	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	33
10^c	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	51
11^d	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	43
12^e	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	50
13^f	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	34
14^g	KI (1.5)	DMSO/AcOH (V∶V=1∶1)	34

亚磺酸钠盐和芳基乙酮/茚酮合成β-酮砜

Synthesis of β-Ketosulfone from Sodium Sulfinate and Aryl Ethyl Ketone/Indanone

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