Rhodium(I)-Catalyzed Carbonylative Annulation of Iodobenzenes with Strained Olefins and 4-Octyne in the Presence of Furfural Involving ortho-C–H Bond Cleavage

Takuma Furusawa, Hiroki Tanimoto, Yasuhiro Nishiyama, Tsumoru Morimoto*, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

The rhodium(I)-catalyzed carbonylative annulation of iodobenzenes with strained olefins in the presence of furfural as a carbonyl source, accompanied by ortho-C–H bond cleavage, is reported. The use of 4-octyne in place of strained olefins also leads to the formation of the corresponding inden-9-one. The timely release of the carbonyl moiety via the rhodium-catalyzed decarbonylation of furfural plays a decisive role in this reaction. (Figure presented.).

Original languageEnglish
Pages (from-to)240-245
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number2
DOIs
StatePublished - 2017/01/19

Keywords

  • C–H functionalization
  • carbonylative annulation
  • furfural
  • rhodium catalyst
  • three-component reactions

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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