Rhodium(III)-Catalyzed Tandem [2+2+2] Annulation–Lactamization of Anilides with Two Alkynoates via Cleavage of Two Adjacent C−H or C−H/C−O bonds

Miho Fukui, Yu Shibata, Yuki Hoshino, Haruki Sugiyama, Kota Teraoka, Hidehiro Uekusa, Keiichi Noguchi, Ken Tanaka

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

An electron-deficient CpE rhodium(III) complex bearing a cyclopentadienyl ligand with two ethyl ester substituents catalyzes the tandem [2+2+2] annulation–lactamization of acetanilides with two alkynoates via cleavage of adjacent two C−H bonds to give densely substituted benzo[cd]indolones. The reactions of meta-methoxy-substituted acetanilides with two alkynoates also provided benzo[cd]indolones via cleavage of adjacent C−H/C−O bonds. Furthermore, 3,5-dimethoxyacetanilides reacted with two alkynoates to give dearomatized spiro compounds.

Original languageEnglish
Pages (from-to)2260-2264
Number of pages5
JournalChemistry - An Asian Journal
Volume11
Issue number16
DOIs
Publication statusPublished - 2016 Aug 19
Externally publishedYes

Keywords

  • alkynes
  • anilides
  • annulation
  • benzo[cd]indolones
  • rhodium

ASJC Scopus subject areas

  • Chemistry(all)

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