Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters

doi:10.6023/cjoc202206023

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 756-762.DOI: 10.6023/cjoc202206023 Previous Articles Next Articles

α-酮酸与硫酚的电化学脱羧偶联: 一种合成硫代酸酯的新方法

黄嘉为, 李潇漫, 徐亮, 韦玉^*()

石河子大学化学化工学院新疆兵团化工绿色过程重点实验室新疆石河子 832003

收稿日期:2022-09-06 修回日期:2022-09-21 发布日期:2022-10-31
基金资助:
国家自然科学基金(22061036)

Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters

Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei()

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2022-09-06 Revised:2022-09-21 Published:2022-10-31
Contact: *E-mail: yuweichem@shzu.edu.cn
Supported by:
National Natural Science Foundation of China(22061036)

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Abstract

Thioester compounds have been widely applied in the synthesis of bioactive chemicals, natural products and organic materials due to their versatile reactivities. In recent years, the decarboxylation coupling reactions between α-keto acids and thiols/thiophenols have been utilized to access thioesters. Herein, an electrochemical decarboxylation coupling method has been established, which uses α-keto acids and thiophenols as the starting materials and affords thioesters in moderate to good yields. This protocol features simple manipulation and avoids usually needed metal-based catalysts, bases or external oxidants, thus providing a new, mild, and green pathway to synthesize thioester compounds.

Key words: electrochemical synthesis, α-keto acid, thiophenol, thioester

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Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei. Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 756-762.

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Fig. & Tab. 6

References 32

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Entry	Variations from optimal conditions	Yield^b/%
1	None	90
2	without electrical current	N.D. ^c
3	2.0 equiv. of 2a	88
4	without TFA	55
5	pivalic acid instead of TFA	70
6	C/C instead of Pt/Pt	Trace
7	C/Pt instead of Pt/Pt	trace
8	Without H₂O	53
9	MeCN instead of DMSO	12
10	DCM instead of DMSO	N.D.^c
11	DMF instead of DMSO	84
12	28 h instead of 24 h	89
13	20 h instead of 24 h	78

Entry	Variations from optimal conditions	Yield^b/%
1	None	90
2	without electrical current	N.D. ^c
3	2.0 equiv. of 2a	88
4	without TFA	55
5	pivalic acid instead of TFA	70
6	C/C instead of Pt/Pt	Trace
7	C/Pt instead of Pt/Pt	trace
8	Without H₂O	53
9	MeCN instead of DMSO	12
10	DCM instead of DMSO	N.D.^c
11	DMF instead of DMSO	84
12	28 h instead of 24 h	89
13	20 h instead of 24 h	78

α-酮酸与硫酚的电化学脱羧偶联: 一种合成硫代酸酯的新方法

Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters

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References 32

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