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Dehydrogenation of the NH−NH Bond Triggered by Potassium tert ‐Butoxide in Liquid Ammonia
Author(s) -
Wang Lei,
Ishida Akiko,
Hashidoko Yasuyuki,
Hashimoto Makoto
Publication year - 2017
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.201610371
Subject(s) - dehydrogenation , chemistry , phenylhydrazine , ammonia , potassium , yield (engineering) , organic chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
A novel strategy for the dehydrogenation of the NH−NH bond is disclosed using potassium tert ‐butoxide ( t BuOK) in liquid ammonia (NH 3 ) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one‐pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.