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

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

Research output: Article

14 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 - júl. 14 2009

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ASJC Scopus subject areas

  • Organic Chemistry

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