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.

The Co(porphyrin) catalysed reaction of dihydronaphthalene with ArN3, instead affording the corresponding amine, yields the benzylic amine of tetrahydronaphthalene. The amination occurs with the concomitant reduction of dihydronaphthalene due to the reactivity of the endocyclic CC bond coupled with the hydrogen donor capability of dihydronaphthalene. Two reaction mechanisms are proposed.Figure optionsDownload as PowerPoint slideHighlights
► The Co(porphyrin) catalysed amination of dihydronaphthalene was reported.
► The amination occurs with the concomitant reduction of dihydronaphthalene and the consequent formation of the amine of tetrahydronaphthalene.
► Proposed mechanisms for the dihydronaphthalene amination are depicted.