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A Click Chemistry Approach to Tetrazoles by Huisgen 1,3‐Dipolar Cycloaddition: Synthesis of 5‐Sulfonyl Tetrazoles from Azides and Sulfonyl Cyanides
Author(s) -
Demko Zachary P.,
Sharpless K. Barry
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020617)41:12<2110::aid-anie2110>3.0.co;2-7
Quantitative yields are observed from the reaction of aryl sulfonyl cyanides with unhindered azides by simply heating at 80–100°C (see scheme). The reactions are run neat, and there are no by‐products, so no workup is necessary. The resulting tetrazoles are activated for rapid functionalization by an S N Ar reaction.