Iridium-Catalyzed Intramolecular Methoxy C−H Addition to Carbon–Carbon Triple Bonds

Direct Synthesis of 3-Substituted Benzofurans from o-Methoxyphenylalkynes

Takeru Torigoe, Toshimichi Ohmura, Michinori Suginome

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C−H bond of a methoxy group in 1-methoxy-2-(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p-xylene at 135 °C in the presence of an iridium catalyst. The initial 5-exo cyclization products underwent double-bond migration during the reaction to give 3-(arylmethyl)benzofurans in high yields.

Original languageEnglish
Pages (from-to)10415-10419
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number30
DOIs
Publication statusPublished - Jan 1 2016

Fingerprint

Benzofurans
Methyl Ethers
Iridium
Alkynes
Cyclization
Toluene
Xylene
Benzene
Ethers
Catalysts
4-xylene

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Iridium-Catalyzed Intramolecular Methoxy C−H Addition to Carbon–Carbon Triple Bonds : Direct Synthesis of 3-Substituted Benzofurans from o-Methoxyphenylalkynes. / Torigoe, Takeru; Ohmura, Toshimichi; Suginome, Michinori.

In: Chemistry - A European Journal, Vol. 22, No. 30, 01.01.2016, p. 10415-10419.

Research output: Contribution to journalArticle

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