Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through β-hydride elimination/hydrorhodation sequence

Masahiko Shimada, Tatsuro Harumashi, Tomoya Miura, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Methoxy-substituted 1,6-enynes react with arylboronic acids in the presence of a rhodium(I)complex to give arylated cyclization products. This occurs by a multi-step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, β-hydride elimination, hydro-rhodation, and β-oxygen elimination. A shift of the position of a carbon-carbon double bond is observed, suggesting that the β-hydride elimination/hydrorhodation process is repeatedly taking place.

Original languageEnglish
Pages (from-to)1035-1040
Number of pages6
JournalChemistry - An Asian Journal
Volume3
Issue number6
DOIs
Publication statusPublished - Jun 2 2008
Externally publishedYes

Keywords

  • Boron
  • Catalysis
  • Cyclization
  • Elimination
  • Rhodium

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Organic Chemistry

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