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Synthesis of Diarylalkanes by Photoreductive 1,2-Diarylation of Alkenes with Aryl Halides and Cyanoaromatics

Liang Zeng, Xuan‐Hui Ouyang, Deliang He, Jin‐Heng Li

2024The Journal of Organic Chemistry15 citationsDOI

Abstract

We report a visible light-induced photoreductive strategy for three-component diarylation of alkenes with aryl halides and cyanoaromatics. Upon photoredox catalysis and with tertiary alkyl amines as the electron transfer agent, aryl halides selectively undergo halogen atom transfer to generate the aryl radicals and two C(sp 2 )–C(sp 3 ) bonds between the cabron atoms are created in a radical addition and radical–radical coupling fashion to rapidly assemble diverse functionalized polyarylalkanes with high regio- and chemoselectivity. This method can be applied to broad feedstocks, including terminal alkenes, internal alkenes, aryl iodides, aryl bromides, aryl chlorides, electron-deficient benzonitriles, and isonicotinonitriles.

Topics & Concepts

HalideArylChemistryHalogenAlkylCatalysisPhotochemistryElectron transferPhotoredox catalysisAryl radicalRadicalCombinatorial chemistryOrganic chemistryPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques