Reductive Azidation of Carbonyl Compounds via Tosylhydrazone Intermediates Using Sodium Azide | Zendy

Barluenga José | Zendy; TomásGamasa María | Zendy; Valdés Carlos | Zendy

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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).

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