Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis

Alexandra R. Rivero, Peter Fodran, Alica Ondrejkova, Carl-Johan Wallentin*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

30 Citations (Scopus)

Abstract

A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1 degrees, 2 degrees, and 3 degrees alcohols and allows their use in the functionalization of C(sp(3))-H and C(sp(2))-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.

Original languageEnglish
Pages (from-to)8436-8440
Number of pages5
JournalOrganic letters
Volume22
Issue number21
DOIs
Publication statusPublished - 6-Nov-2020
Externally publishedYes

Keywords

  • STEREOSELECTIVE-SYNTHESIS
  • HYDROGEN-ATOM
  • ARYL ETHERS
  • FUNCTIONALIZATION
  • CYCLIZATION
  • OXIDATION
  • RING

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