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Updated: Sep 18, 2025

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Zinc-Promoted Synthesis of β-(Thio)uredo-Sulfides from Isothiocyanates and Tertiary Amines
Pankaj Kumar1, Jaswinder Kaur1, Aman Bhalla1
1Department of Chemistry, Panjab University Chandigarh, Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University Chandigarh, Union Territory, 160014, India.
Abstract:
Herein, we highlight the sequential Zn-promoted reactivity of isothiocyanates towards tertiary aliphatic amines with subsequent regioselective N-dealkylation, yielding respective thioureas. Under non-inert conditions Zn functions as a desulfurizing agent affording ZnS, while water acts as an oxygen source, facilitating the direct transformation of isothiocyanates into ureas. This strategy affords b-(thio)uredo-sulphides, important functionalities in synthetic and biological important functionalities. Through a comprehensive examination of the mechanism and substrate scope, we elucidate a non-radical pathway with Hofmann elimination as initial and desulfurization as final steps.
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