C-N Bond Cleavage of Anilines by a (Salen)ruthenium(VI) Nitrido Complex

We report experimental and computational studies of the facile oxidative C-N bond cleavage of anilines by a (salen)rutheniurn(VI) nitrido complex. We provide evidence that the initial step involves nucleophilic attack of aniline at the nitrido ligand of the ruthenium complex, which is followed by proton and electron transfer to afford a (salen)ruthenium(II) diazonium intermediate. This intermediate then undergoes unimolecular decomposition to generate benzene and N-2.