Rhodium-catalyzed (5+1) annulations between 2-alkenylphenols and allenes: A practical entry to 2,2-disubstituted 2H-chromenes

Noelia Casanova, Andrés Seoane, José L. Mascareñas, Moisés Gulías

Research output: Indexed journal article Articlepeer-review

116 Citations (Scopus)

Abstract

Readily available alkenylphenols react with allenes under rhodium catalysis to provide valuable 2,2-disubstituted 2H-chromenes. The whole process, which involves the cleavage of one C-H bond of the alkenyl moiety and the participation of the allene as a one-carbon cycloaddition partner, can be considered a simple, versatile, and atom-economical (5+1) heteroannulation. The reaction tolerates a broad range of substituents both in the alkenylphenol and in the allene, and most probably proceeds through a mechanism involving a rhodium-catalyzed C-C coupling followed by two sequential pericyclic processes.

Original languageEnglish
Pages (from-to)2374-2377
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number8
DOIs
Publication statusPublished - 16 Feb 2015
Externally publishedYes

Keywords

  • Allenes
  • Annulations
  • C-H activation
  • Reaction mechanisms
  • Rhodium

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