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  • Title: Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer.
    Author: Tsui E, Metrano AJ, Tsuchiya Y, Knowles RR.
    Journal: Angew Chem Int Ed Engl; 2020 Jul 13; 59(29):11845-11849. PubMed ID: 32227658.
    Abstract:
    We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII -based photoredox catalyst, a Brønsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, 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.
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