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Chretien, J.-M., Kerric, G., Zammattio, F., Galland, N., Paris, M., Quintard, J.-P. & Le Grognec, E. (2019) Tin-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures. Advanced Synthesis & Catalysis, 361 747–757.
Added by: Richard Baschera (2019-03-26 10:55:33) Last edited by: Richard Baschera (2019-03-26 11:01:23) |
| Type de référence: Article DOI: 10.1002/adsc.201801117 Clé BibTeX: Chretien2019 Voir tous les détails bibliographiques  |
Catégories: IMN Créateurs: Chretien, Galland, Kerric, Le Grognec, Paris, Quintard, Zammattio Collection: Advanced Synthesis & Catalysis |
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| Résumé |
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The preparation of 5-substituted 1H-tetrazoles was efficiently achieved by reaction of trimethylsilylazide with nitriles using a triorganotin alkoxide precatalyst. The reaction mechanism was first investigated using a homogeneous tributyltin derivative and was explored through experimental investigations and DFT calculations. A heterogeneous version was then developed using a polymer-supported organotin alkoxide and afforded an efficient method for the preparation of tetrazoles in high yields with an easy work-up and a residual tin concentration in the desired products compatible for pharmaceutical applications (less than
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