AuCl-catalyzed reaction of ortho-alkynyl(oxo)benzene with benzenediazonium 2-carboxylate as a synthetic method towards anthracene, triptycene, and phthalazine derivatives

Kenichiro Sato, Menggenbateer, Toshihiko Kubota, Naoki Asao

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The AuCl-catalyzed benzannulation of ortho-alkynylphenyl ketones with benzenediazonium 2-carboxylate proceeded efficiently at 40 °C in (CH2Cl)2 and a variety of anthracene derivatives, having a ketone group at 9-position, were produced in good to high yields. On the other hand, the reaction of ortho-alkynylbenzaldehydes with benzenediazonium 2-carboxylate afforded triptycyl ketones. The reactions most probably proceed through the formation of a zwitterionic intermediate by the gold-induced electrophilic cyclization of ortho-alkynyl(oxo)benzenes, followed by the cycloaddition of benzyne. In contrast, when the above reaction was carried out at rt in 1,4-dioxane, phthalazine derivative was produced without the generation of benzyne.

Original languageEnglish
Pages (from-to)787-796
Number of pages10
JournalTetrahedron
Volume64
Issue number5
DOIs
Publication statusPublished - 2008 Jan 28
Externally publishedYes

Keywords

  • Anthracene
  • Benzannulation
  • Benzyne
  • Gold catalyst

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'AuCl-catalyzed reaction of ortho-alkynyl(oxo)benzene with benzenediazonium 2-carboxylate as a synthetic method towards anthracene, triptycene, and phthalazine derivatives'. Together they form a unique fingerprint.

Cite this