Oxidative addition of arylhalogen bonds of N-benzylidenbenzylamines to palladium(0) compounds

Abstract

The oxidative addition of imines 2-Cl,6-XC 6H 3CHNCH 2C 6H 4-2′-Y, (X  H, Cl; Y  Cl, Br) and 4-NO 2C 6H 4CHNCH 2C 6H 4-2′-Br to [Pd(PPh 3) 4] and [Pd(dba) 2] has been studied. endo Cyclometallated compounds are obtained if the carbonhalogen bonds to be activated are the same in both aromatic rings, and the exo derivatives are obtained only if the benzylic phenyl ring contains an ortho-CBr bond. The activation of the stronger CCl bond, with formation of an endocyclic compound, takes place in preference to that of the weaker CBr bond when the imine 2,6-Cl 2C 6H 3CHNCH 2C 6H 4-2′-Br reacts with [Pd(PPh 3) 4].