Palladium-catalyzed intramolecular arylation reaction:: Mechanism and application for the synthesis of polyarenes

The intramolecular palladium-catalyzed reaction of aryl bromides and triflates with arenes has been used for the preparation of polyarenes. The synthesis of benz[e]acephenantrylenes, corannulenes, and C60H30, a 'crushed fullerene', by using this methodology are presented. Mechanistic studies on the arylation step point to an electrophilic substitution reaction pathway. 1 Introduction 2 An Approach to the Synthesis of Fullerene Fragments based on the Palladium-Catalyzed Arylation 3 Synthesis of Benz [e] acephenantrylenes and Related Polyarenes by Palladium-Catalyzed Arylation 4 An Approach to the Synthesis of Dibenzocorannulene 5 Mechanistic Insights into the Palladium-Catalyzed Arylation Reaction 5.1 The Role of Phosphine Ligands 5.2 Electrophilic Substitution or C-H Activation? 6 Palladium Catalyzed Arylation Synthesis of C-3h Polyarenes from Truxenes 7 Summary and Outlook.