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Copper-Catalyzed Formal Dehydrogenative Coupling of Carbonyls with Polyfluoroarenes Leading to β-C–H Arylation

Weilong Xie, Dongwook Kim, Sukbok Chang

2020Journal of the American Chemical Society48 citationsDOI

Abstract

We herein communicate a formal dehydrogenative coupling of carbonyls with polyfluoroarenes enabled by Cu catalysis. Silyl enol ethers initially prepared from carbonyls are postulated to undergo the copper-mediated oxidative dehydrogenative coupling with polyfluoroarenes via a radical pathway. Including cyclic and linear ketones, aldehydes, and esters, a broad range of β-aryl carbonyl products were efficiently obtained in high regio- and stereoselectivity with excellent functional group tolerance.

Topics & Concepts

ChemistryCatalysisArylEnolRegioselectivitySilylationCopperStereoselectivityOrganic chemistryCombinatorial chemistryMedicinal chemistryAlkylCatalytic C–H Functionalization MethodsFluorine in Organic ChemistryRadical Photochemical Reactions
Copper-Catalyzed Formal Dehydrogenative Coupling of Carbonyls with Polyfluoroarenes Leading to β-C–H Arylation | Litcius