A Direct Arylation-Cyclisation Reaction for the Construction of Medium-Sized Rings.

A strategy for assembling biaryls linked through a medium-sized ring is herein presented. π-Complexation of fluoroarenes to chromium tricarbonyl activates the molecule towards both C-H activation and nucleophilic aromatic substitution without covalently altering the molecular connectivity of the arene. The construction of bridged biaryl molecules with 6-10-membered core rings is achieved through a one-pot C-H arylation/nucleophilic aromatic substitution sequence. The methodology is applicable to the synthesis of heterocyclic as well as fully carbocyclic rings.