Rhodium(III)-Catalyzed Annulation of 2-Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2-Substituted Indolines

Marc Font, Borja Cendón, Andrés Seoane, José Luis Mascareñas, Moisés Gulías

Research output: Indexed journal article Articlepeer-review

60 Citations (Scopus)

Abstract

A RhIII complex featuring an electron-deficient η5-cyclopentadienyl ligand catalyzed an unusual annulation between alkynes and 2-alkenyl anilides to form synthetically appealing 2-substituted indolines. Formally, the process can be viewed as an allylic amination with concomitant hydrocarbonation of the alkyne. Mechanistic experiments indicate that this transformation involves an unusual rhodium migration with a concomitant 1,5-H shift.

Original languageEnglish
Pages (from-to)8255-8259
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number27
DOIs
Publication statusPublished - 2 Jul 2018
Externally publishedYes

Keywords

  • annulation
  • C−H activation
  • indolines
  • rhodium
  • rhodium shift

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