Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines
                                
                                    
                                        作者:Robert J. Perry、S. Richard Turner                                    
                                    
                                        DOI:10.1021/jo00023a023
                                    
                                    
                                        日期:1991.11
                                    
                                    A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines.  Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115-degrees-C, 90 psi of CO, 3% PdCl2L2, and 2.4 equiv of DBU.  This process is tolerant of a wide variety of functional groups and gives good yields of the desired products.  Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction.  The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.