ORGN 177

N-Benzyl and N-phenethyl amide arene ruthenium complexes participate in intramolecular nucleophilic aromatic addition and nucleophilic aromatic substitution as a function of side chain identity.  Products of the former reaction manifold can be efficiently converted to spiro- or fused-ring bicyclic materials upon oxidative demetalation.  Thus, ruthenium-based methods provide facile access to azaspiro[4.5]decane, tetrahydroisoquinoline, and 3-benzazepine derivatives.  Factors influencing the regioselectivity of aromatic addition, as well as the scope, limitations, and synthetic potential of these processes will be discussed.