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.
Authors
- Yanmin Huang
- Yan‐Hong He (ORCID: https://orcid.org/0000-0002-6405-285X)
- Jiayi Luo (ORCID: https://orcid.org/0000-0002-5038-719X)
- Yu‐Fang Tan (ORCID: https://orcid.org/0000-0002-2707-9092)
- Zhi Guan (ORCID: https://orcid.org/0000-0002-0369-6141)
Institutions
- Southwest University (CN)
- Ingenierie des Materiaux polymeres (FR)
- Nanning Normal University (CN)
- Chongqing Municipal Government (CN)
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
- Field-Weighted Citation Impact
- 0.00