Abstract
AbstractA multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N‐chlorophthalimide (NCPI) system is described to selectively obtain non‐aromatic five‐membered sulfur heterocycles (1,3‐oxathiol‐2‐imines/thiazol‐2(3H)‐one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional‐group tolerance, high regio‐ and chemo‐ selectivities, gram‐scale synthesis and late‐stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free‐radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3‐oxathiol‐2‐imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn‐off” response, demonstrating potential applications in environmental and biological fields.
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