Tin‐Catalyzed Synthesis of 5‐Substituted 1H‐Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures. Issue 4 (20th December 2018)

• Record Type: Journal Article
• Authors: Chrétien, Jean‐Mathieu; Kerric, Gaelle; Zammattio, Françoise; Galland, Nicolas; Paris, Michael; Quintard, Jean‐Paul; Le Grognec, Erwan
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 4(2019)
• Page Start: 747
• Page End: 757
• Publication Date: 2018-12-20
• Subjects: Azides -- Stannanes -- Tin -- Cycloaddition -- Solid-phase synthesis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201801117
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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 10 ppm). Abstract :