PtCl2-catalyzed cyclization of o-diethynylbenzene derivatives triggered by intramolecular nucleophilic attack

Koji Miki, Hiroyuki Kuge, Rui Umeda, Motohiro Sonoda, Tobe Yoshito*

*Corresponding author for this work

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

(Chemical Equation Presented) PtCl2-catalyzed cyclization of o-diethynylbenzene derivatives bearing a hydroxyethyl group yielded naphthofuran derivatives by initial intramolecular cyclization of the hydroxy group to an activated ethynyl group followed by attack of the second ethynyl group to a vinylplatinum intermediate. When the ethynyl terminal is substituted by a hydroxypropyl group, not only homologous naphthodihydropyran but also indenylidenete-trahydrofuran derivatives were formed.

Original languageEnglish
Pages (from-to)1077-1087
Number of pages11
JournalSynthetic Communications
Volume41
Issue number7
DOIs
StatePublished - 1 Jan 2011

Keywords

  • Cyclization
  • Dihydronaphthofuran
  • Lewis acid
  • Nucleophilic addition
  • o-diethynylbenzene

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