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Reductive Azidation of Carbonyl Compounds via Tosylhydrazone Intermediates Using Sodium Azide
Author(s) -
Barluenga José,
TomásGamasa María,
Valdés Carlos
Publication year - 2012
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.201200313
Subject(s) - sodium azide , cycloaddition , chemistry , azide , alkyl , alkyne , combinatorial chemistry , scheme (mathematics) , organic chemistry , catalysis , mathematics , mathematical analysis
Simple and direct : Aldehydes and ketones can be transformed into alkyl azides through a reductive coupling of the corresponding tosylhydrazones in a process that takes place simply in the presence of K 2 CO 3 , tetrabutylammonium bromide (TBAB), and NaN 3 (top of scheme). The application of this methodology followed by the Cu‐catalyzed azide–alkyne cycloaddition allows the direct transformation of carbonyl compounds into triazoles (bottom of scheme).