Synthetic Communications p. 1534 - 1548 (2009)
Update date:2022-08-04
Topics:
Takacs, Attila
Abreu, Artur R.
Peixoto, Andreia F.
Pereira, Mariette
Kollar, Laszlo
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. Copyright Taylor & Francis Group, LLC.
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