Chemoselective Aryl–Aryl Coupling through C–F Bond Activation

Key words

C–C coupling - buckybowls - C–F activation

Significance

Bowl-shaped polycyclic aromatic hydrocarbons have emerged as intriguing building blocks for organic electronic materials. The large strain induced by the curved π-system has thus far only been overcome under harsh conditions that are intolerant to functional groups. In this work, the authors demonstrate directed intramolecular aryl–aryl coupling through C–F bond activation.

Comment

This aryl–aryl coupling method selectively activated C–F bonds in the presence of other halogens, thus allowing further modification after the cyclization. Yields are near quantitative and operationally facile. Several crystal structures have been obtained and properties evaluated through DFT studies.