Work

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

Year: 2020

Type: article

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 Ir III ‐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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202003959

Authors: Elaine Tsui, Anthony J. Metrano, Yuto Tsuchiya, Robert R. Knowles

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Affordable and clean energy

Open Access status: green

Funder: National Institute of General Medical Sciences