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

[Image: see text] 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 cond...

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Autores principales: Altarejos, Julia, Merino, Estíbaliz, Sucunza, David, Vaquero, Juan J., Carreras, Javier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407847/
https://www.ncbi.nlm.nih.gov/pubmed/37478336
http://dx.doi.org/10.1021/acs.joc.3c00396
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author Altarejos, Julia
Merino, Estíbaliz
Sucunza, David
Vaquero, Juan J.
Carreras, Javier
author_facet Altarejos, Julia
Merino, Estíbaliz
Sucunza, David
Vaquero, Juan J.
Carreras, Javier
author_sort Altarejos, Julia
collection PubMed
description [Image: see text] 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.
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spelling pubmed-104078472023-08-09 One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives Altarejos, Julia Merino, Estíbaliz Sucunza, David Vaquero, Juan J. Carreras, Javier J Org Chem [Image: see text] 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. American Chemical Society 2023-07-21 /pmc/articles/PMC10407847/ /pubmed/37478336 http://dx.doi.org/10.1021/acs.joc.3c00396 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Altarejos, Julia
Merino, Estíbaliz
Sucunza, David
Vaquero, Juan J.
Carreras, Javier
One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives
title One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives
title_full One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives
title_fullStr One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives
title_full_unstemmed One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives
title_short One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives
title_sort one-pot (3 + 2) cycloaddition–isomerization–oxidation of 2,2,2-trifluorodiazoethane and styryl derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407847/
https://www.ncbi.nlm.nih.gov/pubmed/37478336
http://dx.doi.org/10.1021/acs.joc.3c00396
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