Copper(I)-Catalyzed Cycloaddition of 4‑Bromosydnones and Alkynes for the Regioselective Synthesis of 1,4,5-Trisubstituted Pyrazoles

Copper(I)-Catalyzed Cycloaddition of 4‑Bromosydnones and Alkynes for the Regioselective Synthesis of 1,4,5-Trisubstituted Pyrazoles

Copper-catalyzed cycloaddition of alkynes with 4-bromosydnones provides a convenient, mild, and regioselective method for the synthesis of a wide range of bromopyrazoles. The broad functional group tolerance of the cycloaddition reaction and further palladium-catalyzed cross-coupling reactions allow...

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Bibliographic Details
Published in:Organic letters Vol. 17; no. 2; pp. 362 - 365
Main Authors: Decuypere, Elodie, Specklin, Simon, Gabillet, Sandra, Audisio, Davide, Liu, Hui, Plougastel, Lucie, Kolodych, Sergii, Taran, Frédéric
Format: Journal Article
Language:English
Published: United States American Chemical Society 16-01-2015
Subjects:
Alkynes - chemistry
Catalysis
Copper - chemistry
Cycloaddition Reaction
Molecular Structure
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Stereoisomerism
Sydnones - chemistry
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Summary:Copper-catalyzed cycloaddition of alkynes with 4-bromosydnones provides a convenient, mild, and regioselective method for the synthesis of a wide range of bromopyrazoles. The broad functional group tolerance of the cycloaddition reaction and further palladium-catalyzed cross-coupling reactions allowed the preparation of polyfunctionalized 1,4,5-pyrazoles that are otherwise difficult to obtain by conventional methods.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol503482a