The Transition Metal-catalyzed N-Alkylation and N-heterocyclization. A Reductive Transformation of Nitroarenes into (Dialkylamino)arenes and 2,3-Dialkyl-substituted Quinolines Using Aliphatic Aldehydes under Carbon Monoxide

Article abstract of DOI:10.1246/bcsj.55.1116

The catalytic N-alkylation and N-heterocyclization of nitroarenes occur at 180 deg C under a carbon monoxide pressure of 70 atm and in the presence of aldehyde and such transitionmetal complexes as rhodium and palladium complexes, thus giving 2,3-dialkyl-substituted quinolines and (dialkylamino)arenes in good yields.The product selectivity depends greatly on the catalysts: a binary catalyst, RhCl(PPh3)3 and PdCl2, is effective for the N-heterocyclization, while is effective for the N-alkylation.