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Mechanochemical Iridium(III)-Catalyzed B-Amidation of <i>o</i>-Carboranes with Dioxazolones

Gi Uk Han, Seohyun Shin, Yonghyeon Baek, Dongwook Kim, Kooyeon Lee, Jeung Gon Kim, Phil Ho Lee

2021Organic Letters41 citationsDOI

Abstract

Mechanochemistry was successfully applied to the functionalization of carboranes. The mechanochemical iridium(III)-catalyzed regioselective B(3)- and B(4)-amidation of unsubstituted o-carboranes with dioxazolones was developed. In addition, the mechanochemical iridium(III)-catalyzed regioselective B(4)-amidation of substituted o-carboranes was demonstrated. Because mechanochemical B-amidation proceeds smoothly without organic solvents or external heating, the present method is regarded as a sustainable and environmentally friendly surrogate for typical solvent-based reactions.

Topics & Concepts

IridiumRegioselectivityChemistryMechanochemistryCatalysisSurface modificationEnvironmentally friendlyOrganic chemistrySolventCombinatorial chemistryPhysical chemistryBiologyEcologyBoron Compounds in ChemistryOrthopedic Infections and TreatmentsRadiopharmaceutical Chemistry and Applications
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