Bottom-up Construction of Graphene Segments Based on a Palladium-Catalyzed Annulative Dimerization of o-Iodobiaryl Compounds.


A straightforward method based on a Pd-catalyzed annulative dimerization of o-iodobiaryl compounds via a double C-I and C-H bond cleavage for the construction of aromatic compounds with a triphenylene core has been developed. The protocol features simple reaction conditions that require neither a ligand nor an oxidant, and it tolerates a wide scope of coupling partners without compromising its efficiency or scalability. More importantly, the generated TCCT synthon can be used to prepare a series of fully fused, small graphene nanoribbons by a late-stage arylation with arylboronic acids and subsequent Scholl reaction. Thus, our synthetic strategy allows bottom-up access to these extended π-systems in a controlled manner.


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