Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes

Ulrich Hennecke presents the dichlorination of unfunctionalized alkenes through organocatalysis.

The dihalogenation of alkenes is a very old reaction, one of the fundamental processes of organic chemistry that is usually taught to undergraduates in an introductory organic chemistry course. Professor Ulrich Hennecke from the Vrije Universiteit Brussel (Belgium) referred to the suggestion of Robert and Kimball in 1937 that these reactions could proceed via cyclic halonium ions and therefore the mechanism is well understood. Indeed, the mechanism involving the haliranium ion is found in most organic chemistry textbooks presenting the prime example of an electrophilic addition reaction supposed to proceed via a cyclic halonium ion, explaining the usually observed anti-addition of the two halogen atoms. However, things are not always as straightforward as originally thought, and a group of researchers led by Professor Hennecke has been investigating the reaction from a novel angle.

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