Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides

Co(porphyrin) complexes promote an unusual reactivity of dihydronaphthalene towards several aryl azides. The reaction affords the benzylic amine of tetrahydronaphthalene instead yielding the amine of dihydronaphthalene as it normally happens in the presence of Ru(porphyrin)CO catalysts. The amination process occurs with the concomitant reduction of the dihydronaphthalene double bond probably due to the high reactivity of the endocyclic CC bond coupled with the good hydrogen donor capability of dihydronaphthalene. Two mechanisms for this reaction are proposed. © 2012 Elsevier B.V. All rights reserved.