Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 3, Pages 870-873Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610371
Keywords
azo compounds; dehydrogenation; photoaffinity labeling; small ring compounds; synthetic methods
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Funding
- Grants-in-Aid for Scientific Research [17K01940] Funding Source: KAKEN
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A novel strategy for the dehydrogenation of the NH-NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH3) 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.
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