There are over 2,000 natural products in the literature containing a chlorine or bromine bearing stereocenter. The synthesis of these heterodihalogenated natural products is synthetically very challenging—especially when molecules that are unfunctionalized are taken into consideration. Many natural products that scientists are interested in possess halogens throughout the molecule. Currently in the literature, there are very few straightforward methods to achieve the proper stereochemistry for dihalogenated natural products. Many of these polyhalogenated natural products also show biological and anti-cancer activity, which have yet to be studied. Herein I propose a catalytic method to induce heterodihalogenation on unfunctionalized dienes and alkenes. This chemistry involves the use of an electrophilic halogenating source and a nucleophilic halogenating source to isolate regiospecific products. Future directions for the application of this dihalogenation method are described towards the synthesis of various biologically active natural products.

Heterodihalogenation of alkenes and dienes

ACS Spring 2022

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