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Cu 2 (OTf) 2 ‐Catalyzed and Microwave‐Controlled Preparation of Tetrazoles from Nitriles and Organic Azides under Mild, Safe Conditions
Author(s) -
Bosch Lluís,
Vilarrasa Jaume
Publication year - 2007
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/anie.200605095
Subject(s) - cycloaddition , catalysis , microwave , microwave heating , chemistry , organic synthesis , polar effect , organic chemistry , combinatorial chemistry , computer science , telecommunications
Avoiding hazards : Cu 2 (OTf) 2 ⋅C 6 H 6 (OTf=O 3 SCF 3 ) is the catalyst of choice for the [3+2] cycloaddition of organic azides and ethyl cyanoformate or related nitriles (see scheme; PG=protecting group, EWG=electron‐withdrawing group). For the first time, tetrazoles are obtained from these substrates at room temperature; heating at 80 °C in CH 2 Cl 2 (microwave reactor) is only required for the most reluctant substrates.