Tris (trimethylsilyl) silane and azobis (cyclohexanenitrile) promoted the easy intramolecular arylation of aryl bromopyridine carbamates through a radical [1, 6] ipso substitution process. These substrates showed a preference for this type of reaction over the alternative [1, 7] addition. The results were rationalized by making use of quantum mechanical calculations and computer graphics.