Arylsulfenylation of 4-thiazolidinone with elemental sulfur and aryl halide: Thioether linkage (C–S–C)

• Published in: Tetrahedron Vol. 156; p. 133947
• Main Authors: Patel, Dixita J., Chikhalia, Kishor H.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 28-04-2024
• Subjects: 4-Thiazolidinone; Arylsulfenylation; Copper(I)iodide; C–S–C bond formation; Elemental sulfur; Elemental sulfur; Arylsulfenylation; Copper(I)iodide; C–S–C bond formation; 4-Thiazolidinone
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2024.133947

The generation of carbon–sulfur (C–S) bonds is a crucial step in the quest to create valuable organic entities due to their widespread applications in various biological systems. Alongside, 4-thiazolidinone is considered a highly proficient heterocyclic scaffold, constituting diversified pharmacological properties. It has driven us to develop a one-pot synthesis of thioarylated 4-thiazolidinones with elemental sulfur and aryl halides using copper(I) iodide as catalyst. The method has a broad substrate scope with various substituted aryl halides. Optimization has been carried out through different catalyst loadings, base, temperature and solvent. The reaction is highly efficient and affords thioarylated 4-thiazolidinones in good yields with broad functional group tolerance.
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