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

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Authors
Altarejos Salido, JuliaUniversity of Alcalá Author; Merino Marcos, EstibalizUniversity of Alcalá Author; Sucunza Saenz, DavidUniversity of Alcalá Author; Vaquero Lopez, Juan JoseUniversity of Alcalá Author; Carreras Perez Aradros, JavierUniversity of Alcalá Author
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/57890
DOI: 10.1021/acs.joc.3c00396
ISSN: 0022-3263
Date
2023-07-21
Academic Departments
Universidad de Alcalá. Departamento de Química Orgánica y Química Inorgánica
Teaching unit
Unidad docente Química Orgánica
Funders
Ministerio de Ciencia e Innovación
Instituto de Salud Carlos III
Comunidad de Madrid
Bibliographic citation
The Journal of Organic Chemistry, 2023, v. 88, n. 15, p. 11258-11262
Project
info:eu-repo/grant/Agreement/MICINN//PID2019-105007GA-I00/ES//
info:eu-repo/grant/Agreement/ISCIII//RD21/0005/0005/ES//
info:eu-repo/grant/Agreement/CAM//2018-T1%2FIND-10054/CM%2FJIN%2F2021-007
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
© The authors
Attribution 4.0 International (CC BY 4.0)
Access rights
info:eu-repo/semantics/openAccess
Abstract
A facile access to5-aryl-3-trifluoromethylpyrazoles has been developedby a one-pot (3 + 2) cycloaddition-isomerization-oxidationsequence employing 2,2,2-trifluorodiazoethane and styryl derivatives.A broad variety of functional groups and good yields are achievedunder mild conditions. Additionally, the functionalization of 3-trifluoromethylpyrazoleswas studied. DFT calculations of the cycloaddition transition stateenergies are consistent with the experimentally observed reactivity.

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