A new approach to seven, eight and nine membered ring synthesis involving a radical ipso-substitution is described. The method involves treatment of a 2-iodobenzyl-indanone or tetralone with tributyltin hydride and AIBN. Addition of the resulting aryl radical to the pendant carbocycle then occurred in a 5-exo-trig manner to the ring junction. Fragmentation of the resulting radical intermediate lead to rearomatisation of the arene and to the formation of a highly stabilised radical. With tetralone derivatives the 5-exo-trig ipso-cyclisation completed with 6-endo/exo-ortho-addition while in the case of benzocyclobutane a competing 5-exo trig cyclisation to a nitrile was observed in addition to the formation of the seven membered ring. A study on the use of tetrakistrimethylsilyl silane-TBAF for the reduction of the aryl halides is also presented.