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Photocatalytic Hydroalkylation of Aryl-Alkenes

Cornelia S. Buettner, Michael Schnürch, Katharina Bica

2022The Journal of Organic Chemistry16 citationsDOIOpen Access PDF

Abstract

Here, we present a visible light-catalyzed hydroalkylation of aryl-alkenes affording C-C bonds using aryl-alkenes and alkyl iodides. We demonstrate the formation of various hydroalkylation products in excellent yields, with primary, secondary, and tertiary alkyl iodides being tolerated in the reaction. Mechanistic experiments reveal a pathway consisting of halogen atom transfer followed by a radical-polar crossover mechanism delivering the desired hydroalkylation products.

Topics & Concepts

ChemistryArylAlkylHalogenPhotocatalysisOrganic chemistryCombinatorial chemistryCatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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