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Tin‐Catalyzed Synthesis of 5‐Substituted 1 H ‐Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures
Author(s) -
Chrétien JeanMathieu,
Kerric Gaelle,
Zammattio Françoise,
Galland Nicolas,
Paris Michael,
Quintard JeanPaul,
Le Grognec Erwan
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801117
Subject(s) - tin , alkoxide , homogeneous , tributyltin , chemistry , derivative (finance) , catalysis , combinatorial chemistry , organic chemistry , mathematics , financial economics , economics , combinatorics
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).