Palladium‐Catalyzed Carbonylation of 4‐Substituted 2‐Iodoaniline Derivatives: Carbonylative Cyclization and Aminocarbonylation.

Abstract

Carbonylation O 0305Palladium-Catalyzed Carbonylation of 4-Substituted 2-Iodoaniline Derivatives: Carbonylative Cyclization and Aminocarbonylation. -Iodoanilines (I) and various primary or secondary amines, including amino acid esters, undergo an aminocarbonylation reaction with double CO insertion at the iodo-substituted position to give 2-ketocarboxamides. In the absence of nucleophiles like amines or alcohols, anilines (I) undergo two types of 'dimeric' intramolecular aminocarbonylation reactions, depending on the substituents, to give benzoxazine derivatives (IX) or diazocine derivatives (X). -(ACS, P.; MUELLER, E.; RANGITS, G.; LORAND, T.; KOLLAR*, L.; Tetrahedron 62 (2006) 51, 12051-12056; Dep. Inorg. Chem., Janus Pannonius Univ., H-7624 Pecs, Hung.; Eng.) -Klein 13-041