Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 72, Pages 18161-18165Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201705442
Keywords
C-H amination; charge-transfer complexes; electron-deficient arenes; heterocycles; photocatalysis
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Funding
- Deutsche Forschungsgemeinschaft [GRK 1626]
- European Research Council (ERCadv grant Pharos)
- Alexander von Humboldt (AvH) foundation
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The C-H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH(2) as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.
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