Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts

Andrés Seoane, Cezar Comanescu, Noelia Casanova, Rebeca García-Fandiño, Xabier Diz, José L. Mascareñas, Moisés Gulías

Research output: Indexed journal article Articlepeer-review

31 Citations (Scopus)

Abstract

o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C−H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc) 2 .

Original languageEnglish
Pages (from-to)1700-1704
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number6
DOIs
Publication statusPublished - 4 Feb 2019
Externally publishedYes

Keywords

  • anilides
  • annulation
  • C−H activation
  • naphthylamines
  • rhodium

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