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Photoinduced N-Heterocyclic Nitrenium-Catalyzed Single Electron Reduction of Acyl Fluorides for Phenanthridine Synthesis

Lei Bao, Zhixiang Wang, Xiang‐Yu Chen

2023Organic Letters36 citationsDOI

Abstract

Acyl fluorides are versatile reagents in organic synthesis. However, there is no precedent to employ acyl fluorides as acyl radical precursors. We herein report an N-heterocyclic nitrenium iodide salt-catalyzed photoreduction of acyl fluorides to produce acyl radicals, which could react with 2-isocyanobiaryls to afford various carbonyl phenanthridines.

Topics & Concepts

ChemistryPhenanthridineCatalysisRadicalReagentNucleophilic acyl substitutionIodideSalt (chemistry)Organic synthesisAcylationCombinatorial chemistryOrganic chemistryPhotochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Photoinduced N-Heterocyclic Nitrenium-Catalyzed Single Electron Reduction of Acyl Fluorides for Phenanthridine Synthesis | Litcius