Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 17, Pages 5342-5345Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600783
Keywords
enzyme models; flavins; oxidative; chlorination photocatalysis
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [GRK 1626]
- Fonds der Chemischen Industrie
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Chlorine gas or electropositive chlorine reagents are used to prepare chlorinated aromatic compounds, which are found in pharmaceuticals, agrochemicals, and polymers, and serve as synthetic precursors for metal-catalyzed cross-couplings. Nature chlorinates with chloride anions, FAD-dependent halogenases, and O-2 as the oxidant. A photocatalytic oxidative chlorination is described based on the organic dye riboflavin tetraacetate mimicking the enzymatic process. The chemical process allows within the suitable arene redox potential window a broader substrate scope compared to the specific activation in the enzymatic binding pocket.
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