High-yielding synthesis of 1-carboxamido-3,4-dihydronaphthalenes via palladium-catalyzed aminocarbonylation

Roland Farkas, Erik A. Molnár, Péter Ács, Attila Takács, László Kollár

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2 Citations (Scopus)

Abstract

1-Iodo-3,4-dihydronaphthalene, an iodoalkene substrate obtained from α-tetralon, has been carbonylated in the presence of palladiumephosphine precatalysts. Systematic investigations have revealed that the 1-carboxamido-3,4-dihydronaphthalenes and 1-methoxycarbonyl-3,4- dihydronaphthalene have been formed in exceptionally high isolated yields (up to 96%) in chemospecific reaction. The influence of the amine nucleophile and that of the reaction conditions (carbon monoxide pressure, reaction temperature) on the reactivity of the substrate have been investigated.

Original languageEnglish
Pages (from-to)500-504
Number of pages5
JournalTetrahedron
Volume69
Issue number2
DOIs
Publication statusPublished - Jan 14 2013

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Keywords

  • Amine nucleophile
  • Carbon monoxide
  • Carbonylation
  • Homogeneous catalysis
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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