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

preprint
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.

History

Email Address of Submitting Author

elaine.tsui@princeton.edu

Institution

Princeton University

Country

United States

ORCID For Submitting Author

0000-0002-5872-4824

Declaration of Conflict of Interest

No conflict of interest.

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