From Reactive Oxygen Species to Reactive Brominating Species: Fenton Chemistry for Oxidative Bromination
Guodong Zhao, Eryu Wang, Rongbiao Tong
Abstract
Fenton chemistry (FeII + H2O2 → HO•/HOO• + H2O) generates reactive oxygen species (ROS) that are used for treatment of wastewater and oxidation of organic molecules and play a key role in biological oxidation systems. This study shows that Fenton chemistry can be used for generation of reactive brominating species (RBS) under neutral conditions at room temperature. The in situ RBS are successfully used for three types of oxidative bromination reactions. This green and nonacidic new method addresses the safety and environmental challenges of existing oxidative bromination methods. Additionally, this neutral Fenton–bromide system addresses the long-lasting problem of many functional haloperoxidase mimics that required strong acids for oxidation of bromide ion with hydrogen peroxide. This new green and mild method for generating RBS will significantly benefit the wide applications of brominated organic compounds in organic synthesis and the fine chemical and pharmaceutical industries.