Regio- and stereoselective synthesis of ( E)-3-arylmethyleneisoindolin-1-ones via Pd(II)/Cu(II)-catalyzed one-pot C-C/C-N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency. Further elaboration of the products obtained from this process enabled very short and efficient syntheses of aristolactam and indoloisoquinolinone alkaloids.