HFIP-Promoted Synthesis of Substituted Tetrahydrofurans by Reaction of Epoxides with Electron-Rich Alkenes
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Título: | HFIP-Promoted Synthesis of Substituted Tetrahydrofurans by Reaction of Epoxides with Electron-Rich Alkenes |
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Autor/es: | Llopis, Natalia | Baeza, Alejandro |
Grupo/s de investigación o GITE: | Alternative Methodologies In Chemistry (AMIC) |
Centro, Departamento o Servicio: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Palabras clave: | Tetrahydrofuranes | Fluorinated alcohols | Green chemistry |
Área/s de conocimiento: | Química Orgánica |
Fecha de publicación: | 30-jul-2020 |
Editor: | MDPI |
Cita bibliográfica: | Llopis N, Baeza A. HFIP-Promoted Synthesis of Substituted Tetrahydrofurans by Reaction of Epoxides with Electron-Rich Alkenes. Molecules. 2020; 25(15):3464. https://doi.org/10.3390/molecules25153464 |
Resumen: | In the present work, the employment of fluorinated alcohols, specifically 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), as solvent and promoter of the catalyst-free synthesis of substituted tetrahydrofuranes through the addition of electron-rich alkenes to epoxydes is described. The unique properties of this fluorinated alcohol, which is very different from their non-fluorinated analogs, allows carrying out this new straightforward protocol under smooth reaction conditions affording the corresponding adducts in moderate yields in the majority of cases. Remarkably, this methodology has allowed the synthesis of new tetrahydrofuran-based spiro compounds as well as tetrahydrofurobenzofuran derivatives. The scope and limitations of the process are also discussed. Mechanistic studies were also performed pointing towards a purely ionic or a SN2-type process depending on the nucleophilicity of the alkene employed. |
Patrocinador/es: | This research was funded by the Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P and CTQ2017-88171-P) and Spanish Ministerio de Ciencia, Innovación y Universidades (PGC2018-096616-B-I00) and the University of Alicante (UADIF17-27, VIGROB-285, VIGROB-316/19, UADIF19-106) and we would like to thank them for the financial support. |
URI: | http://hdl.handle.net/10045/108571 |
ISSN: | 1420-3049 |
DOI: | 10.3390/molecules25153464 |
Idioma: | eng |
Tipo: | info:eu-repo/semantics/article |
Derechos: | © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
Revisión científica: | si |
Versión del editor: | https://doi.org/10.3390/molecules25153464 |
Aparece en las colecciones: | INV - AMIC - Artículos de Revistas |
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