Palladium-catalysed selective aminocarbonylation of 1′,4-diiodostyrene

Antal Szilágyi, Roland Farkas, Andrea Petz, L. Kollár

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

1′,4-Diiodostyrene possessing both iodo-aryl and iodo-alkenyl functionalities was prepared and used as substrate in palladium-catalysed aminocarbonylation. The corresponding dicarboxamides were obtained as major products in high yields by using several amine nucleophiles including amino acid methyl esters. Due to the highly different reactivity of the two iodo-functionalities, the selective aminocarbonylation of the iodo-vinyl moiety was carried out at atmospheric carbon monoxide pressure resulting in the formation of 4-iodo-phenyl-acrylamides. The latter amides were used as substrates in high pressure aminocarbonylation resulting in amide-ketocarboxamide type products. The latter functionality was formed via double carbon monoxide insertion into the iodo-aryl bond.

Original languageEnglish
Pages (from-to)4484-4489
Number of pages6
JournalTetrahedron
Volume65
Issue number23
DOIs
Publication statusPublished - Jun 6 2009

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Palladium
Carbon Monoxide
Amides
Acrylamides
Pressure
Nucleophiles
Substrates
Amines
Esters
Amino Acids

Keywords

  • Amino acid
  • Aminocarbonylation
  • Carbon monoxide
  • Diiodostyrene
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalysed selective aminocarbonylation of 1′,4-diiodostyrene. / Szilágyi, Antal; Farkas, Roland; Petz, Andrea; Kollár, L.

In: Tetrahedron, Vol. 65, No. 23, 06.06.2009, p. 4484-4489.

Research output: Contribution to journalArticle

Szilágyi, Antal ; Farkas, Roland ; Petz, Andrea ; Kollár, L. / Palladium-catalysed selective aminocarbonylation of 1′,4-diiodostyrene. In: Tetrahedron. 2009 ; Vol. 65, No. 23. pp. 4484-4489.
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