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Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer

submitted on 15.01.2020 and posted on 20.01.2020 by Elaine Tsui, Anthony J. Metrano, Yuto Tsuchiya, Robert Knowles
We report a light-driven, catalytic protocol for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible light irradiation in the presence of an Ir(III)-based photosensitizer, a Brønsted base catalyst, and a hydrogen atom transfer co-catalyst. Reactive alkoxy radicals are proposed as key intermediates that are generated by direct homolytic activation of alcohol O–H bonds through a proton-coupled electron transfer mechanism. This method exhibits a broad substrate scope and high functional group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.


Email Address of Submitting Author


Princeton University


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest.