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

Edon Vitaku, Jon T. Njardarson

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


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
Issue number22
StatePublished - Aug 2016


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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry


Dive into the research topics of 'A Mild meta-Selective C–H Alkylation of Catechol Mono-Ethers'. Together they form a unique fingerprint.

Cite this