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• W2256861716 abstract "Acid-catalyzed electrophilic aromatic substitution for C-C bond formation, commonly referred to as the Friedel-Crafts reaction in recognition of its discoverers, has been one of the most useful reactions in organic chemistry for over a century. However, the Friedel-Crafts reaction cannot occur on a benzene ring having a strongly electron withdrawing group, such as an acyl group, which deactivates the aromatic ring toward electrophilic substitutions and remains a major challenge. Herein, the synthesis of naphthoquinones and 1,3-indandiones, bearing two acyl groups at positions ortho to each other on a benzene ring, are demonstrated by means of copper-catalyzed intramolecular aerobic oxidative acylation of benzoylacetone derivative precursors. This unusual Friedel-Crafts reaction reveals a new activation mode for the in situ polarity reverse of an electron-deficient aromatic ring to a reactive, electron-rich ring tuned by remote electronic effects." @default.
• W2256861716 created "2016-06-24" @default.
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• W2256861716 date "2015-08-11" @default.
• W2256861716 modified "2023-10-16" @default.
• W2256861716 title "Friedel–Crafts Coupling of Electron-Deficient Benzoylacetones Tuned by Remote Electronic Effects" @default.
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• W2256861716 doi "https://doi.org/10.1021/acs.joc.5b01371" @default.
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