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Updated: May 13, 2025

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Published on: May 26, 2019
Mechanochemical Approach for Metal-Free Regioselective C5-Sulfenylation of Imidazo[2,1-b]Thiazoles
Xinya Liu1, Valentin Dorokhov1, Olivier Provot1
1Department of Chemistry, CNRS, BioCIS, Université Paris-Saclay, 91400, Orsay, France.
Abstract:
The development of sustainable and selective methodologies for heterocyclic functionalization remains a key challenge in organic synthesis. In this study, a novel, metal-free bis(trifluoroacetoxy)iodo]benzene-mediated strategy for the regioselective C5-sulfenylation of imidazo[2,1-b]thiazoles using aryl methyl sulfides under mechanochemical conditions is reported. This solvent-free approach offers a rapid, efficient, and environmentally friendly alternative to current methods, achieving yields of up to 86% while completely avoiding hazardous solvents. The method exhibits broad substrate scope, with tolerance to both electron-donating and electron-withdrawing functional groups. This mechanochemical strategy provides a valuable synthetic tool for the functionalization of imidazo[2,1-b]thiazole scaffold, with potential applications in medicinal and materials chemistry.
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