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Halogenase-Inspired Oxidative Chlorination Using Flavin Photocatalysis.


ABSTRACT: 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 O2 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.

SUBMITTER: Hering T 

PROVIDER: S-EPMC5069574 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Halogenase-Inspired Oxidative Chlorination Using Flavin Photocatalysis.

Hering Thea T   Mühldorf Bernd B   Wolf Robert R   König Burkhard B  

Angewandte Chemie (International ed. in English) 20160317 17


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 O2 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 t  ...[more]

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