A combination of DFT and kinetic studies suggests a mechanism for olefin aziridination by organic azides catalysed by ruthenium porphyrins

Ferretti, F.

Gallo, E.

Manca, G.

Mealli, C.

Pozzoli, A.

Zardi, P.

Dalton Transactions

English

A mechanism for the aziridination of olefins by aryl azides (ArN3), promoted by ruthenium(ii) porphyrin complexes, is proposed on the basis of kinetic and theoretical studies. All the recorded data support the involvement of a mono-imido ruthenium complex as the active intermediate in the transfer of the nitrene moiety "ArN" to the olefin. The selectivity of the aziridination vs. the uncatalysed triazoline formation can be enhanced by fine-tuning the electronic features of the porphyrin ligand and the olefin/azide catalytic ratio. The DFT study highlights the importance of an accessible triplet ground state of the intermediate ruthenium mono-imido complex to allow the evolution of the aziridination process

P. Zardi

A. Pozzoli

F. Ferretti

G. Manca

C. Mealli

E. Gallo

AIR Universita degli studi di Milano

A mechanistic investigation of the ruthenium porphyrin catalysed aziridination of olefins by aryl azides

Zardi P.

Pozzoli A.

Ferretti F.

Manca G.

Mealli C.

Gallo E.

Archivio istituzionale della ricerca - Università di Modena e Reggio Emilia

Open Access Repository

A combination of DFT and kinetic studies suggests a mechanism for olefin aziridination by organic azides catalysed by ruthenium porphyrins.</p

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Archivio istituzionale della ricerca - Università di Padova

https://iris.unimore.it/bitstream/11380/1285857/2/c5dt00951k.pdf

A mechanistic investigation of the ruthenium porphyrin catalysed aziridination of olefins by aryl azides

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AIR Universita degli studi di Milano

Archivio istituzionale della ricerca - Università di Modena e Reggio Emilia

Open Access Repository

Crossref

Archivio istituzionale della ricerca - Università di Padova