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Photoredox-Catalyzed Cascade sp<sup>2</sup> C–H Bond Functionalization to Construct Substituted Acridine with Diarylamine and Hypervalent Iodine(III) Reagents

Li Liu, Yage Zhang, Wenyan Zhao, Jin-Xia Wen, Chunping Dong, Caijuan Hu, Jian Li

2023Organic Letters24 citationsDOI

Abstract

C-H bond activation of diarylamines with hypervalent iodine diazo reagents was developed. A variety of diarylamines and hypervalent iodine(III) reagents were tolerated well, and a range of substituted acridines with yields ranging from moderate to excellent was provided efficiently. The protocol introduces diazo groups onto diarylamines and enables subsequent late-stage assembly point functionalization with the diazonium structure, forming two new C-C bonds in a sequential fashion.

Topics & Concepts

Hypervalent moleculeChemistryDiazoReagentSurface modificationIodineCombinatorial chemistryAcridineCatalysisOrganic chemistryPhysical chemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthesis and Catalytic Reactions
Photoredox-Catalyzed Cascade sp<sup>2</sup> C–H Bond Functionalization to Construct Substituted Acridine with Diarylamine and Hypervalent Iodine(III) Reagents | Litcius