Rhodium-catalyzed carbonylative annulation of 2-bromobenzylic alcohols with internal alkynes using furfural via β-aryl elimination

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

In spite of the significant progress made in transformations of unstrained benzylic (tert-)alcohols through β-aryl elimination, catalytic carbonylation has not yet been developed extensively because alkoxycarbonylation is probably favored over β-aryl elimination. In this letter, we report on the rhodium(I)-catalyzed carbonylative annulation of α,α-dimethyl-(2-bromoaryl)methanols with internal alkynes using furfural leading to the formation of indenones. The key to the success of the reaction is the timely generation of the carbonyl source via the decarbonylation of furfural.

Original languageEnglish
Pages (from-to)926-929
Number of pages4
JournalChemistry Letters
Volume46
Issue number7
DOIs
StatePublished - 2017

Keywords

  • C-C bond cleavage
  • Carbonylative annulations
  • Decarbonylation

ASJC Scopus subject areas

  • General Chemistry

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