Synthesis of ortho-alkoxy-aryl carboxamides via alladium-catalyzed aminocarbonylation

Attila Takács, Artur R. Abreu, Andreia F. Peixoto, Mariette Pereira, L. Kollár

Research output: Article

13 Citations (Scopus)

Abstract

Various aryl carboxamides with alkoxy substituents at the ortho-position, applicable as direct intermediates toward novel ligands, were synthesised via aminocarbonylation of aryl-iodides (2-iodoanisole, 5-chloro-7-iodo-8-methoxy- quinoline, and 5-chloro-7-iodo-8-benzyloxy-quinoline) in the presence of in situ generated palladium(0) catalysts. Simple primary and secondary amines as well as aminoacid esters were used as N-nucleophiles. The optimization of the reaction conditions allowed the preferential formation of carboxamides or ketocarboxamides by simple or double carbon monoxide insertion, respectively. A strong dependence of the chemoselectivity on carbon monoxide pressure was observed.

Original languageEnglish
Pages (from-to)1534-1548
Number of pages15
JournalSynthetic Communications
Volume39
Issue number9
DOIs
Publication statusPublished - 2009

Fingerprint

Carbon Monoxide
Nucleophiles
Palladium
Iodides
Amines
Esters
Ligands
Catalysts
N-(8-aminohexyl)-5-iodonaphthalene-1-sulfonamide
alkoxyl radical
quinoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of ortho-alkoxy-aryl carboxamides via alladium-catalyzed aminocarbonylation. / Takács, Attila; Abreu, Artur R.; Peixoto, Andreia F.; Pereira, Mariette; Kollár, L.

In: Synthetic Communications, Vol. 39, No. 9, 2009, p. 1534-1548.

Research output: Article

Takács, Attila ; Abreu, Artur R. ; Peixoto, Andreia F. ; Pereira, Mariette ; Kollár, L. / Synthesis of ortho-alkoxy-aryl carboxamides via alladium-catalyzed aminocarbonylation. In: Synthetic Communications. 2009 ; Vol. 39, No. 9. pp. 1534-1548.
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AU - Pereira, Mariette

AU - Kollár, L.

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KW - Iodo-aromatics

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