Additive-Free Synthesis of β-Keto Thioesters through Thiocarbonylation of Sulfoxonium Ylides with Thioic acids

doi:10.6023/cjoc202507031

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 578-585.DOI: 10.6023/cjoc202507031 Previous Articles Next Articles

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无添加剂条件下硫叶立德与硫代羧酸硫酯化反应合成β-羰基硫代羧酸酯

杨梓^a^,^*(), 马超^b, 王祖利^d, 魏伟^b^,^*(), 易东^c^,^*()

^a 长沙医学院功能核酸基础与临床湖南省普通高校重点实验室长沙 410219
^b 曲阜师范大学化学与化工学院山东曲阜 273165
^c 西南医科大学药学院四川泸州 646000
^d 南京林业大学林木生物质低碳高效利用国家工程研究中心南京 210037

收稿日期:2025-07-21 修回日期:2025-09-08 发布日期:2025-10-14
通讯作者: 杨梓, 魏伟, 易东
基金资助:
泸州市人民政府西南医科大学科技战略合作(2023LZXNYDJ019)

Additive-Free Synthesis of β-Keto Thioesters through Thiocarbonylation of Sulfoxonium Ylides with Thioic acids

Zi Yang^a^,^*(), Chao Ma^b, Zuli Wang^d, Wei Wei^b^,^*(), Dong Yi^c^,^*()

^a Hunan Provincial University Key Laboratory of the Fundamental and Clinical Research on Functional Nucleic Acid, Changsha Medical University, Changsha 410219
^b School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
^c School of Pharmacy, Southwest Medical University, Luzhou, Sichuan 646000
^d National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037

Received:2025-07-21 Revised:2025-09-08 Published:2025-10-14
Contact: Zi Yang, Wei Wei, Dong Yi
Supported by:
Science and Technology Strategic Cooperation Programs of Luzhou Municipal People’s Government and Southwest Medical University(2023LZXNYDJ019)

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Abstract

A simple and convenient strategy for the synthesis of β-keto thioesters has been developed through the thiocar- bonylation reaction of sulfoxonium ylides with thioic acids. A number of β-keto thioestrs could be efficiently obtained at room temperature with moderate to good yields in the absence of any additives. The reaction could be easily scaled up, which features operational simplicity, mild condition, and good reaction efficiency.

Key words: sulfoxonium ylides, thioic acids, β-keto thioesters, additive-free

Cite this article

Zi Yang, Chao Ma, Zuli Wang, Wei Wei, Dong Yi. Additive-Free Synthesis of β-Keto Thioesters through Thiocarbonylation of Sulfoxonium Ylides with Thioic acids[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 578-585.

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References 16

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Entry	Additive (mol%)	Solvent	Yield^b/%
1	DBU (100)	CH₃CN	82
2	Cs₂CO₃ (100)	CH₃CN	76
3	—	CH₃CN	86
4	CuI (10)	CH₃CN	76
5	I₂ (10)	CH₃CN	80
6	CuSO₄ (10)	CH₃CN	82
7	AgNO₃ (10)	CH₃CN	72
8	—	EtOAc	78
9	—	Toluene	88
10	—	DCE	80
11	—	CH₂Cl₂	84
12	—	1,4-Dioxane	63
13	—	EtOH	72
14	—	Acetone	80
15	—	THF	12
16	—	DMSO	7
17	—	DMF	8
18	—	Toluene	80^c
19	—	Toluene	83^d
20	—	Toluene	82^e

Entry	Additive (mol%)	Solvent	Yield^b/%
1	DBU (100)	CH₃CN	82
2	Cs₂CO₃ (100)	CH₃CN	76
3	—	CH₃CN	86
4	CuI (10)	CH₃CN	76
5	I₂ (10)	CH₃CN	80
6	CuSO₄ (10)	CH₃CN	82
7	AgNO₃ (10)	CH₃CN	72
8	—	EtOAc	78
9	—	Toluene	88
10	—	DCE	80
11	—	CH₂Cl₂	84
12	—	1,4-Dioxane	63
13	—	EtOH	72
14	—	Acetone	80
15	—	THF	12
16	—	DMSO	7
17	—	DMF	8
18	—	Toluene	80^c
19	—	Toluene	83^d
20	—	Toluene	82^e

无添加剂条件下硫叶立德与硫代羧酸硫酯化反应合成β-羰基硫代羧酸酯

Additive-Free Synthesis of β-Keto Thioesters through Thiocarbonylation of Sulfoxonium Ylides with Thioic acids

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