Electrochemical Vicinal Dichlorination and Dibromination of Unactivated Alkenes Using TMSX as the Halogen Source

Abstract

An environmentally friendly electrochemical method for vicinal dichlorination of unactivated alkenes has been developed using TMSCl as a chlorine source, facilitated by Et₄NI-mediated electrophilic addition under undivided electrolytic conditions. This sustainable and clean electrochemical system provides an efficient route to a series of dichloroalkanes. Replacing TMSCl with TMSBr enables the dibromination of unactivated alkenes. Mechanistic experiments indicate that this electrochemical strategy proceeds via an ionic process, where in situ generation of iodide ions and subsequent chlorination reactions drive the formation of dichloroalkanes.