α-Functionalization of ketones in an umpolung fashion can be achieved by nucleophilic addition to the oxy-allyl cation intermediate. However, applicable carbon nucleophiles are limited to ones with high nucleophilicity. Additionally, introduction of a leaving group to the α-position of ketone substrates is required beforehand. Herein, we report the CuCl2 -mediated oxidative intramolecular α-arylation of ketones with less nucleophilic phenolic moieties as carbon nucleophiles via α-chlorination of ketones and the subsequent generation of the oxy-allyl cation intermediates, giving ketones with a quaternary carbon center at the α-position.
Keywords: arylation; halogenation; ketones; quaternary stereocenters; umpolung.
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