Palladium-catalysed aminocarbonylation/cyclization of iodoalkenes toward N-propargylcarboxamides and oxazoles

Péter Szuroczki, Gábor Mikle, L. Kollár

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Palladium(0) complexes formed in situ from a palladium(II) precursor, Pd(OAc)2, proved to be highly active catalytic system in aminocarbonylation of the variety of iodoalkenes (1-iodocyclohexene, 4-tert-butyl-1-iodocyclohexene, 2-methyl-1-iodocyclohexene, α-iodostyrene, 2-iodobornene, 17-iodoandrost-16-ene, 17-iodo-3-methoxyestra-1,3,5(10),16-tetraene, 20-iodo-3β-hydroxypregna-5,20-diene) using propargylamine and its derivatives as N-nucleophile. While the carboxamides formed from the parent propargylamine and its 1,1-dimethyl substituted derivative underwent palladium-catalysed ring-closure reaction resulting in the corresponding oxazoles and oxazolines, respectively, the carboxamides formed from N-methylpropargylamine are reluctant toward any cyclization.

Original languageEnglish
Pages (from-to)68-74
Number of pages7
JournalMolecular Catalysis
Volume452
DOIs
Publication statusPublished - Jun 1 2018

Fingerprint

Oxazoles
oxazole
Cyclization
Palladium
palladium
Derivatives
Nucleophiles
nucleophiles
dienes
closures
rings
propargylamine

Keywords

  • Aminocarbonylation
  • Carbon monoxide
  • Carboxamide
  • Oxazole
  • Propargylamine

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

Cite this

Palladium-catalysed aminocarbonylation/cyclization of iodoalkenes toward N-propargylcarboxamides and oxazoles. / Szuroczki, Péter; Mikle, Gábor; Kollár, L.

In: Molecular Catalysis, Vol. 452, 01.06.2018, p. 68-74.

Research output: Contribution to journalArticle

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N2 - Palladium(0) complexes formed in situ from a palladium(II) precursor, Pd(OAc)2, proved to be highly active catalytic system in aminocarbonylation of the variety of iodoalkenes (1-iodocyclohexene, 4-tert-butyl-1-iodocyclohexene, 2-methyl-1-iodocyclohexene, α-iodostyrene, 2-iodobornene, 17-iodoandrost-16-ene, 17-iodo-3-methoxyestra-1,3,5(10),16-tetraene, 20-iodo-3β-hydroxypregna-5,20-diene) using propargylamine and its derivatives as N-nucleophile. While the carboxamides formed from the parent propargylamine and its 1,1-dimethyl substituted derivative underwent palladium-catalysed ring-closure reaction resulting in the corresponding oxazoles and oxazolines, respectively, the carboxamides formed from N-methylpropargylamine are reluctant toward any cyclization.

AB - Palladium(0) complexes formed in situ from a palladium(II) precursor, Pd(OAc)2, proved to be highly active catalytic system in aminocarbonylation of the variety of iodoalkenes (1-iodocyclohexene, 4-tert-butyl-1-iodocyclohexene, 2-methyl-1-iodocyclohexene, α-iodostyrene, 2-iodobornene, 17-iodoandrost-16-ene, 17-iodo-3-methoxyestra-1,3,5(10),16-tetraene, 20-iodo-3β-hydroxypregna-5,20-diene) using propargylamine and its derivatives as N-nucleophile. While the carboxamides formed from the parent propargylamine and its 1,1-dimethyl substituted derivative underwent palladium-catalysed ring-closure reaction resulting in the corresponding oxazoles and oxazolines, respectively, the carboxamides formed from N-methylpropargylamine are reluctant toward any cyclization.

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KW - Propargylamine

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