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I<sub>2</sub>/DMSO-Promoted Synthesis of Diaryl Sulfide- and Selenide-Embedded Arylhydrazones

Arun Dhurey, Subhro Mandal, Animesh Pramanik

2023The Journal of Organic Chemistry13 citationsDOI

Abstract

Functionalization and derivatization of arylhydrazones are important in pharmaceutical, medicinal, material, and coordination chemistry. In this regard, a facile I 2 /DMSO-promoted cross-dehydrogenative coupling (CDC) for direct sulfenylation and selenylation of arylhydrazones has been accomplished utilizing arylthiols/arylselenols at 80 °C. This method provides a metal-free benign route for the synthesis of a variety of arylhydrazones embedded with diverse diaryl sulfide and selenide moieties in good to excellent yield. In this reaction, molecular I 2 acts as a catalyst, and DMSO is utilized as a mild oxidant as well as solvent to produce several sulfenyl and selenyl arylhydrazones through a CDC-mediated catalytic cycle.

Topics & Concepts

SelenideYield (engineering)ChemistrySulfideCatalysisDerivatizationCombinatorial chemistrySolventOrganic chemistrySeleniumMaterials scienceMetallurgyHigh-performance liquid chromatographySulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods
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