Electrochemical Coupling of the Sulfonic Acid Sodium and Tertiary Amines for the Synthesis ofβ-Amidovinyl Sulfones

doi:10.6023/cjoc202012051

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2735-2742.DOI: 10.6023/cjoc202012051 Previous Articles Next Articles

Special Issue: 有机电合成虚拟专辑

ARTICLES

苯亚磺酸钠和叔胺电化学耦合生成β-氨基乙烯砜

熊云奎^a^,^b^,^*(), 张健叶^a, 申裙^b, 黄嘉宇^b, 王涛^a^,^b^,^*()

a 江西师范大学国家单糖化学合成工程技术研究中心南昌 330022
b 江西师范大学化学化工学院南昌 330022

收稿日期:2020-12-30 修回日期:2021-03-07 发布日期:2021-04-16
通讯作者: 熊云奎, 王涛

Electrochemical Coupling of the Sulfonic Acid Sodium and Tertiary Amines for the Synthesis ofβ-Amidovinyl Sulfones

Yunkui Xiong^a^,^b(), Jianye Zhang^a, Qun Shen^b, Jiayu Huang^b, Tao Wang^a^,^b()

a National Research Center for Carbohydrate Synthesis, Jiangxi Province Key Laboratory of Chemical Biology,Jiangxi Normal University, Nanchang 330022
b College of Chemistry and Chemical Engineering, Jiangxi Normal university, Nanchang 330022

Received:2020-12-30 Revised:2021-03-07 Published:2021-04-16
Contact: Yunkui Xiong, Tao Wang

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Abstract

β-Amido sulfone motif reprents a particularly useful scaffold for the biologically active molecules. The hydrogenation ofβ-amidovinyl sulfon is an alternative method to synthesizeβ-amido sulfone. Herein, one electrochemical method to synthesizeβ-amido sulfone using sodium sulfites and tertiary amines as substrates is presented. OnlyE-configurations ofβ-amidovinyl sulfonyl were synthesized under metal catalyst- and oxidant-free condition. Cyclic voltammetry (CV) and control experiments indicate that this electrosynthesis reaction goes through a radical process which the sulfonyl radical adds to enamine to form the carbon radical.

Key words: β-amido sulfone, β-amidovinyl sulfon, sodium sulfites, tertiary amines

Cite this article

Yunkui Xiong, Jianye Zhang, Qun Shen, Jiayu Huang, Tao Wang. Electrochemical Coupling of the Sulfonic Acid Sodium and Tertiary Amines for the Synthesis ofβ-Amidovinyl Sulfones[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2735-2742.

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Fig. & Tab. 9

References 27

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Entry	Variation form standard condition	yieldb/%
1	None	92 (83^c)
2	ⁿBu₄NBF₄ instead ofⁿBu₄NOAc	80
3	NaI instead ofⁿBu₄NOAc	80
4	THF/MeOH (V/V=9 mL/1 mL) as solvent	88
5	CH₃CN/AcOH (V/V=9 mL/0.5 mL) as solvent	N.d.^d
6	THF/H₂O (V/V=9 mL/1 mL) as solvent	47
7	CH₃CN (10 mL) as solvent	85
8	Air instead of N₂	42
9	Pt(+)\|Pt(–) instead of C(+)\|Pt(–)	60
10	Ni(+)\|Pt(–) instead of C(+)\|Pt(–)	35
11	Fe(+)\|Pt(–) instead of C(+)\|Pt(–)	Trace
12	without electric current	N.d.^d

Entry	Variation form standard condition	yieldb/%
1	None	92 (83^c)
2	ⁿBu₄NBF₄ instead ofⁿBu₄NOAc	80
3	NaI instead ofⁿBu₄NOAc	80
4	THF/MeOH (V/V=9 mL/1 mL) as solvent	88
5	CH₃CN/AcOH (V/V=9 mL/0.5 mL) as solvent	N.d.^d
6	THF/H₂O (V/V=9 mL/1 mL) as solvent	47
7	CH₃CN (10 mL) as solvent	85
8	Air instead of N₂	42
9	Pt(+)\|Pt(–) instead of C(+)\|Pt(–)	60
10	Ni(+)\|Pt(–) instead of C(+)\|Pt(–)	35
11	Fe(+)\|Pt(–) instead of C(+)\|Pt(–)	Trace
12	without electric current	N.d.^d

苯亚磺酸钠和叔胺电化学耦合生成β-氨基乙烯砜

Electrochemical Coupling of the Sulfonic Acid Sodium and Tertiary Amines for the Synthesis ofβ-Amidovinyl Sulfones

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References 27

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