Litcius/Paper detail

C−H Fluoromethoxylation of Arenes by Photoredox Catalysis

Giulia Bertoli, Ángel Manu Martínez, Jonas F. Goebel, Debora Belmonte, Nardana Sivendran, Lukas J. Gooßen

2022Angewandte Chemie International Edition25 citationsDOIOpen Access PDF

Abstract

Abstract Redox‐active N ‐(fluoromethoxy)benzotriazoles were made accessible from fluoroacetic acid and hydroxybenzotriazoles via electrodecarboxylative coupling. After alkylation, they become effective monofluoromethoxylation reagents, enabling the photocatalytic C−H functionalization of arenes. Thus, irradiation of 1‐(OCH 2 F)‐3‐Me‐6‐(CF 3 )benzotriazolium triflate with blue LED light in the presence of [Ru(bpy) 3 (PF 6 ) 2 ] promotes the synthesis of diversely functionalized aryl monofluoromethyl ethers. This method allows the late‐stage functionalization of biologically relevant structures without relying on ecologically problematic halofluorocarbons.

Topics & Concepts

Photoredox catalysisSurface modificationTrifluoromethanesulfonateAlkylationChemistryCatalysisPhotocatalysisReagentArylCombinatorial chemistryBlue lightRedoxPhotochemistryOrganic chemistryAlkylMaterials sciencePhysical chemistryOptoelectronicsFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
C−H Fluoromethoxylation of Arenes by Photoredox Catalysis | Litcius