Dibenzofuran Synthesis: Decarbonylative Intramolecular C−H Arylation of Aromatic Esters

Toshimasa Okita, Masaaki Komatsuda, Ami N. Saito, Tomoya Hisada, Tomoaki T. Takahara, Keito P. Nakayama, Ryota Isshiki, Ryosuke Takise, Kei Muto, Junichiro Yamaguchi

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A method to provide dibenzofurans through decarbonylative C−H arylation is described. Diaryl ethers bearing an ester functional group, which can be readily prepared by a SNAr reaction, underwent intramolecular C−H arylation in the presence of a palladium catalyst to afford the corresponding dibenzofurans. Electron-rich bis(dialkylphosphine)s such as dcype were critical as the ligand, otherwise the reactions did not proceed at all. This is the first example of C−H arylation of aromatic esters with simple arenes utilized in intramolecular fashion.

Original languageEnglish
Pages (from-to)1358-1361
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume7
Issue number7
DOIs
Publication statusPublished - 2018 Jul

Keywords

  • C−H activation
  • decarbonylation
  • dibenzofurans
  • ethers
  • palladium

ASJC Scopus subject areas

  • Organic Chemistry

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