Homogeneous catalytic aminocarbonylation of 1-iodo-1-dodecene. The facile synthesis of odd-number carboxamides via palladium-catalysed aminocarbonylation

Attila Takács, Péter Ács, Roland Farkas, George Kokotos, L. Kollár

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Various amine nucleophiles including glycine methyl ester were used in the palladium-catalysed aminocarbonylation of (E)- and (Z)-1-iodo-1-dodecene. The substrates were synthesised from 1-dodecanal via the corresponding hydrazone, which was treated with iodine in the presence of tetramethylguanidine. The homogeneous catalytic aminocarbonylation resulted in the corresponding odd-number carboxamides in moderate to good yields. The reaction was accompanied by the formation of some carboxamides with triple bonds in the 2-position. The latter products were formed in relatively high yields with secondary amines such as piperidine and morpholine and were isolated as pure compounds.

Original languageEnglish
Pages (from-to)9874-9878
Number of pages5
JournalTetrahedron
Volume64
Issue number42
DOIs
Publication statusPublished - Oct 13 2008

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Palladium
Amines
Hydrazones
Nucleophiles
Iodine
Substrates
morpholine
glycine methyl ester
piperidine

Keywords

  • Amino acid
  • Aminocarbonylation
  • Carbon monoxide
  • Iodoalkene
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Homogeneous catalytic aminocarbonylation of 1-iodo-1-dodecene. The facile synthesis of odd-number carboxamides via palladium-catalysed aminocarbonylation. / Takács, Attila; Ács, Péter; Farkas, Roland; Kokotos, George; Kollár, L.

In: Tetrahedron, Vol. 64, No. 42, 13.10.2008, p. 9874-9878.

Research output: Contribution to journalArticle

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