Chemoselective reduction of quinols as an alternative to Sonogashira coupling

Synthesis of polysubstituted benzofurans

Youngeun Jung, Ikyon Kim

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

An efficient synthetic approach to polysubstituted benzofurans is described, using 2-methoxyquinone as a benzofuran backbone. Nucleophilic addition of terminal alkynes to 2-methoxy-1,4-benzoquinone afforded the corresponding quinols containing an alkyne unit, which were converted to phenols via mild Zn-mediated reduction. After proper protection of the free phenolic OH, 5-endo-dig iodocyclization allowed facile access to a number of 3-iodobenzofurans. In addition, it was demonstrated for the first time that o-methoxyarylalkynes underwent intramolecular hydroalkoxylation under the influence of AgOTf furnishing the corresponding benzofurans.

Original languageEnglish
Pages (from-to)10454-10472
Number of pages19
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number44
DOIs
Publication statusPublished - 2016 Jan 1

Fingerprint

Benzofurans
Hydroquinones
Alkynes
alkynes
Phenols
quinones
synthesis
phenols

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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Chemoselective reduction of quinols as an alternative to Sonogashira coupling : Synthesis of polysubstituted benzofurans. / Jung, Youngeun; Kim, Ikyon.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 44, 01.01.2016, p. 10454-10472.

Research output: Contribution to journalArticle

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