A Mild meta-Selective C–H Alkylation of Catechol Mono-Ethers

Edon Vitaku, Jon T Njardarson

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Catechol mono-ethers are an important class of phenols. They are found in a number of pharmaceuticals, flavoring agents, perfumes, and are used for the preparation of numerous drugs. Herein, we report a mild meta-selective C–H alkylation of these phenols, which is enabled by a cascade of oxidative dearomatization – radical addition – rearomatization process. The method is compatible with reactive functional groups on the parent arenol, such as olefins and halides. Primary, secondary, and teriary alkyl groups can be used, the source of which is most commonly an alkylborane. This process is operationally simple, does not require heating and generally proceeds in good yields.

Original languageEnglish (US)
Pages (from-to)3679-3683
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number22
DOIs
StatePublished - 2016

Keywords

  • Alkylation
  • C–H substitution
  • Oxidative dearomatization
  • Radicals
  • Regioselectivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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