4.3 Article

Electrochemical bromination of cyclic and acyclic enes using biphasic electrolysis

Journal

SYNTHETIC COMMUNICATIONS
Volume 46, Issue 2, Pages 145-153

Publisher

TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2015.1125498

Keywords

Biphasic media; cyclic and acyclic enes; dibromide; electrolytic oxidation; stereoselectivity

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A simple method of electrochemical bromination of a series of cyclic and acyclic enes (styrene and substituted styrenes, stilbene, indene, and cyclooctene) in a biphasic water-chloroform mixture mediated by bromide/bromine redox system is reported. Aqueous 25% NaBr/H2SO4 is used as the electrolyte. Regio- and stereoselective dibromination of enes is achieved. Moderate to excellent yields of the product (83-98%) is obtained depending on the substrate. Electrolyte reuse has also been demonstrated successfully using HBr in the dibromination of styrene. [GRAPHICS]

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