Development of cross-coupling reactions including electro-oxidative processes and their applications to the synthesis of π-extended compounds

An electrochemical method to synthesize cationic palladium complexes has been developed. Their counter anions could be changed readily by the electrolyte. The reaction could be incorporated into electro - oxidative palladium catalyzed reactions, such as Wacker-type reaction, homo -coupling of arylboronic acids, oxidative Sonogashira-type coupling, and Glaser - type coupling of terminal alkynes. These reactions exhibited a wide scope and a variety of products were obtained in high yields due to high activity of electrogenerated palladium species. We also developed site-selective sequential reactions by the integration of the electro - oxidative coupling reactions with non - electrochemical reactions. The reaction site could be controlled completely by the onloff application of electricity.