Journal
SYNTHETIC COMMUNICATIONS
Volume 39, Issue 9, Pages 1534-1548Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397910802542028
Keywords
Aminocarbonylation; carbon monoxide; carbonylation; iodo-aromatics; palladium; quinoline
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Funding
- Hungarian Research Fund [OTKA NI61591]
- Portuguese FCT [PTDC/QUI/66015/2006]
- European Union [GVOP-3.2.1-2004-04-0168/3]
- [SFRH/BD/29681/2006]
- [SFRH/BD/21314/2005]
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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.
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