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

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

Research output: Contribution to journalArticlepeer-review

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 photo-redox 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.

Original languageEnglish (US)
Pages (from-to)11943-11947
Number of pages5
JournalAdvanced Materials
Volume59
Issue number29
DOIs
StatePublished - 2020

All Science Journal Classification (ASJC) codes

  • Materials Science(all)
  • Mechanics of Materials
  • Mechanical Engineering

Keywords

  • alcohols
  • ethers
  • hydroetherification
  • photocatalysis
  • radicals

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