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Visible-Light-Promoted Iron-Catalyzed <i>N</i>-Arylation of Dioxazolones with Arylboronic Acids

Jingjing Tang, Xiaoqiang Yu, Yoshinori Yamamoto, Ming Bao

2021ACS Catalysis46 citationsDOI

Abstract

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C–N bond construction and nitrene transfer chemistry.

Topics & Concepts

NitreneChemistryCatalysisReactivity (psychology)Functional groupCombinatorial chemistrySubstrate (aquarium)PhotochemistryPhotosensitizerReaction conditionsRadicalOrganic chemistryPolymerOceanographyAlternative medicineGeologyMedicinePathologyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Visible-Light-Promoted Iron-Catalyzed <i>N</i>-Arylation of Dioxazolones with Arylboronic Acids | Litcius