Pyridine-Oriented Transannular C-H Functionalization of Arene

We present a pyridine-oriented transannular Friedel-Crafts alkylation reaction. This reaction, despite being thermodynamically unfavorable, successfully yields a series of pyridine-containing fused seven- or eight-membered rings. The resulting products not only have a similar skeleton to some marketed pharmaceuticals, but also can be further transferred into synthetically promising pleiadienes.