One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives

A facile access to 5-aryl-3-trifluoromethylpyrazoles has been developed by a one-pot (3 + 2) cycloaddition–isomerization–oxidation sequence employing 2,2,2-trifluorodiazoethane and styryl derivatives. A broad variety of functional groups and good yields are achieved under mild conditions. Additional...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-08, Vol.88 (15), p.11258-11262
Main Authors: Altarejos, Julia, Merino, Estíbaliz, Sucunza, David, Vaquero, Juan J., Carreras, Javier
Format: Article
Language:English
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Summary:A facile access to 5-aryl-3-trifluoromethylpyrazoles has been developed by a one-pot (3 + 2) cycloaddition–isomerization–oxidation sequence employing 2,2,2-trifluorodiazoethane and styryl derivatives. A broad variety of functional groups and good yields are achieved under mild conditions. Additionally, the functionalization of 3-trifluoromethylpyrazoles was studied. DFT calculations of the cycloaddition transition state energies are consistent with the experimentally observed reactivity.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00396