General and Mild Palladium-Catalyzed Domino Reaction for the Synthesis of 2H-Indazoles

Practical and highly versatile, the reaction of readily available (2‐chlorophenyl)acetylene and hydrazine substrates affords substituted 2H‐indazoles in just a few hours under very mild reaction conditions (see scheme; DMF=N,N‐dimethylformamide). The catalyzed domino sequence consists of a regiosele...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (37), p.6879-6882
Main Authors: Halland, Nis, Nazaré, Marc, R'kyek, Omar, Alonso, Jorge, Urmann, Matthias, Lindenschmidt, Andreas
Format: Article
Language:English
Subjects:
alkynes
Catalysis
domino reactions
homogeneous catalysis
Indazoles - chemical synthesis
Indazoles - chemistry
nitrogen heterocycles
palladium
Palladium - chemistry
Stereoisomerism
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Summary:Practical and highly versatile, the reaction of readily available (2‐chlorophenyl)acetylene and hydrazine substrates affords substituted 2H‐indazoles in just a few hours under very mild reaction conditions (see scheme; DMF=N,N‐dimethylformamide). The catalyzed domino sequence consists of a regioselective coupling followed by an intramolecular hydroamination and subsequent isomerization of the resulting exocyclic bond.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200902323