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A General and Mild Palladium‐Catalyzed Domino Reaction for the Synthesis of 2 H‐ Indazoles
Author(s) -
Halland Nis,
Nazaré Marc,
R'kyek Omar,
Alonso Jorge,
Urmann Matthias,
Lindenschmidt Andreas
Publication year - 2009
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.200902323
Subject(s) - regioselectivity , palladium , hydroamination , catalysis , domino , intramolecular force , isomerization , chemistry , acetylene , cascade reaction , hydrazine (antidepressant) , amination , dimethylformamide , combinatorial chemistry , sonogashira coupling , medicinal chemistry , organic chemistry , solvent , chromatography
Practical and highly versatile , the reaction of readily available (2‐chlorophenyl)acetylene and hydrazine substrates affords substituted 2 H ‐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.