Palladium-catalysed aminocarbonylation of iodoarenes and iodoalkenes with aminophosphonate as N-nucleophile

Attila Takács, Andrea Petz, L. Kollár

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The high-yielding synthesis of novel N-acyl phosphonates with unprecedented structure was carried out by a homogeneous carbonylation reaction under mild reaction conditions. The palladium-catalysed aminocarbonylation of iodoalkenes (1-iodo-cyclohexene, 1-iodo-4-tert-butyl-cyclohexene, 1-iodo-2-methyl-cyclohexene and α-iodostyrene) with diethyl α-aminobenzyl-phosphonate as N-nucleophile resulted in the exclusive formation of carboxamides. The same reaction with iodoaromatics (iodobenzene, 2-iodothiophene) provided the corresponding carboxamide in high yields and some 2-keto-carboxamides as side products due to single and double carbon monoxide insertion, respectively.

Original languageEnglish
Pages (from-to)8726-8730
Number of pages5
JournalTetrahedron
Volume64
Issue number37
DOIs
Publication statusPublished - Sep 8 2008

Fingerprint

Organophosphonates
Nucleophiles
Palladium
Carbonylation
Carbon Monoxide
cyclohexene
iodobenzene

Keywords

  • Alkyl phosphonate
  • Aminocarbonylation
  • Carbon monoxide
  • Iodoalkenes
  • Iodoaromatics
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalysed aminocarbonylation of iodoarenes and iodoalkenes with aminophosphonate as N-nucleophile. / Takács, Attila; Petz, Andrea; Kollár, L.

In: Tetrahedron, Vol. 64, No. 37, 08.09.2008, p. 8726-8730.

Research output: Contribution to journalArticle

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