Electrochemical bromofunctionalization of alkenes in a flow reactor. Issue 31 (30th July 2021)

• Record Type: Journal Article
• Authors: Seitz, Jakob; Wirth, Thomas
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 31(2021)
• Page Start: 6892
• Page End: 6896
• Publication Date: 2021-07-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01302e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Electrochemical flow functionalization of alkenes is providing fast and easy access to dibromides or bromohydrins. Abstract : The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, the in situ generation of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.