High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation

摘要: 1-Isoindolinone derivatives were synthesised in high yields (up to 89%) by using 2-iodobenzyl bromide and 2-iodobenzylamine as bifunctional substrates palladium-catalysed carbonylation. Depending on the N-nucleophiles, two types of compounds with bromide: use primary amines, including amino acid methylesters, resulted formation N-substituted 1-isoindolinones, while secondary amines react both benzyl iodoarene moieties resulting corresponding ortho-(N-piperidino/morpholinomethyl)-benzamides. The parent 1-isoindolinone was obtained a facile, highly chemoselective intramolecular aminocarbonylation 2-iodobenzylamine. mechanistic details ring-closure reaction conditions leading side-products are discussed well.