Rhodium-catalyzed cyclization of 1,6-enynes triggered by addition of arylboronic acids

Tomoya Miura, Masahiko Shimada, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

99 Citations (Scopus)

Abstract

1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by β-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.

Original languageEnglish
Pages (from-to)1094-1095
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number4
DOIs
Publication statusPublished - Feb 2 2005
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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