Synthesis of 2,3-disubstituted benzofurans by platinum olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals

Itaru Nakamura, Yuya Mizushima, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

217 Citations (Scopus)

Abstract

The PtCl2-catalyzed cyclization reaction of o-alkynylphenyl acetals 1 in the presence of 1,5-cyclooctadiene produces 3-(α-alkoxyalkyl)benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl)phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl)phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal (1f) in the presence of 2 mol % of platinum(II) chloride and 8 mol % of 1,5-cyclooctadiene in toluene at 30 °C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively.

Original languageEnglish
Pages (from-to)15022-15023
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number43
DOIs
Publication statusPublished - 2005 Nov 2

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Synthesis of 2,3-disubstituted benzofurans by platinum olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals'. Together they form a unique fingerprint.

Cite this