Electrosynthesis of 4-Aryl-2-Thiazolidinone Derivatives from Aryl Alkenes with KSCN and H<sub>2</sub>O

A novel electrochemical method for the direct synthesis of 2-thiazolidinone derivatives is reported. Readily available aryl alkenes, KSCN and H<sub>2</sub>O are utilized as starting materials to produce 4-aryl-2-thiazolidinones in moderate to satisfactory yields. KSCN acts as a radical precursor and nucleophile, while H<sub>2</sub>O participates in the formation of carbamoyl groups, ensuring high atom economy. The reaction proceeds under mild and environmentally friendly conditions, constructing the 2-thiazolidinone heterocycle without the need for metals, catalysts, external oxidants, or sacrificial agents. It exhibits excellent product diversity and functional-group tolerance. The reaction is conducted in an undivided cell under open-air conditions and is operationally simple. Late-stage modification of natural products, and scale-up synthesis further demonstrate the practical application of the method.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-09-16
DOI
https://doi.org/10.1021/acs.joc.5c01602
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Electrosynthesis of 4-Aryl-2-Thiazolidinone Derivatives from Aryl Alkenes with KSCN and H2O

Yanmin Huang, Yan‐Hong He, Jiayi Luo, Yu‐Fang Tan et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Electrosynthesis of 4-Aryl-2-Thiazolidinone Derivatives from Aryl Alkenes with KSCN and H2O

Yanmin Huang, Yan‐Hong He, Jiayi Luo, Yu‐Fang Tan, Zhi Guan
article en

Abstract

A novel electrochemical method for the direct synthesis of 2-thiazolidinone derivatives is reported. Readily available aryl alkenes, KSCN and H<sub>2</sub>O are utilized as starting materials to produce 4-aryl-2-thiazolidinones in moderate to satisfactory yields. KSCN acts as a radical precursor and nucleophile, while H<sub>2</sub>O participates in the formation of carbamoyl groups, ensuring high atom economy. The reaction proceeds under mild and environmentally friendly conditions, constructing the 2-thiazolidinone heterocycle without the need for metals, catalysts, external oxidants, or sacrificial agents. It exhibits excellent product diversity and functional-group tolerance. The reaction is conducted in an undivided cell under open-air conditions and is operationally simple. Late-stage modification of natural products, and scale-up synthesis further demonstrate the practical application of the method.

The Journal of Organic ChemistryVol. 90(38)
Southwest University (CN), Ingenierie des Materiaux polymeres (FR), Nanning Normal University (CN), Chongqing Municipal Government (CN)
Openalex Percentile: Top 81%
Radical Photochemical Reactions
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