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Mechanochemically Induced Thianthrenium Salts-Based Arylation of Diverse Heterocyclic Scaffolds

Raman Kumar, Anoop Sharma, Anoop Sharma, Anuj Sharma, Anuj Sharma

2024ACS Sustainable Chemistry & Engineering12 citationsDOI

Abstract

Herein, a mechanochemically triggered C–H arylation of coumarins, quinoline- N -oxides, and uracil molecules with aryl thianthrenium salts is described. Aryl thianthrenium salts are primarily acknowledged for their expedient reusability and adherence to atom economy principles. Mechanistic studies suggested that mechanical stress promoted the homolytic scission of C–S bond of aryl thianthrenium salts, forming aryl radical intermediate. Later, the aryl radical intermediate is engaged in addition reaction with the above heterocycles, leading to the desired products in good yields. This versatile protocol accommodates a wide range of functional groups and facilitates the synthesis of bioactive compounds and drug molecules.

Topics & Concepts

ArylChemistryQuinolineHomolysisBond cleavageMoleculeCombinatorial chemistryAryl radicalReusabilityHypervalent moleculeRadicalOrganic chemistryCatalysisAlkylReagentComputer scienceProgramming languageSoftwareRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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