Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

C–C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and Application in the Assembly of Polycyclic Aromatic Hydrocarbons

C–C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and Application in the Assembly of Polycyclic Aromatic Hydrocarbons
Wenbin Mao, Chen Zhu
Herein, we disclose a new and efficient synthetic approach to triphenylene-based polycyclic aromatic hydrocarbons (PAHs) from ring-fused benzocyclobutenols (RBCBs) through the cleavage of the C–C σ-bond. Two key transformations are involved: (a) palladium-catalyzed C–C bond (hetero)arylation of RBCBs; and (b) Lewis acid-promoted intramolecular annulation leading to complex polycyclic compounds. A variety of multiply substituted triphenylenes and derivatives are obtained in synthetically useful yields.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01727

DOI: 10.1021/acs.joc.7b01727

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