Lill, Malin, Molloy, Conall, Wheelhouse, Katherine M. P., Edwards, Lee J., Lam, Kevin ORCID: https://orcid.org/0000-0003-1481-9212 and Lundberg, Helena (2026) Electrochemically driven deoxychlorination of aliphatic alcohols via alkoxysulfonium intermediates. Chemical Science. ISSN 2041-6520 (Print), 2041-6539 (Online) (doi:10.1039/D6SC05894A)

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Abstract

Native aliphatic alcohols are highly abundant feedstocks of organic synthesis but remain challenging as alkyl donors. Herein, a new class of electrochemically triggered deoxygenative substitution of aliphatic alcohols is described. In the presence of diphenylsulfide, the protocol furnishes alkyl chloride products under mild conditions and tolerates functional groups such as amines, carbamates, heteroaromatic rings, sulfones and free carboxylic acids. Mechanistic studies indicate that the reaction proceeds via nucleophilic substitution of alkoxysulfonium intermediates with inversion of configuration at the hydroxyl carbon, representing a new avenue for deoxyfunctionalization of aliphatic alcohols under electrochemical conditions.

Item Type:	Article
Uncontrolled Keywords:	electrosynthesis, deoxygenation, chlorination, alkoxysulfonium salt
Subjects:	Q Science > Q Science (General) Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science Faculty of Engineering & Science > School of Science (SCI)
Related URLs:	https://pubs.rsc.org/sc/article/doi/10.1...
Last Modified:	02 Sep 2026 09:17
URI:	https://gala.gre.ac.uk/id/eprint/54315

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