4.6 Article

HFIP-Promoted Synthesis of Substituted Tetrahydrofurans by Reaction of Epoxides with Electron-Rich Alkenes

期刊

MOLECULES
卷 25, 期 15, 页码 -

出版社

MDPI
DOI: 10.3390/molecules25153464

关键词

tetrahydrofuranes; fluorinated alcohols; green chemistry

资金

  1. Spanish Ministerio de Economia, Industria y Competitividad [CTQ2015-66624-P, CTQ2017-88171-P]
  2. Spanish Ministerio de Ciencia, Innovacion y Universidades [PGC2018-096616-B-I00]
  3. University of Alicante [UADIF17-27, VIGROB-285, VIGROB-316/19, UADIF19-106]

向作者/读者索取更多资源

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 S(N)2-type process depending on the nucleophilicity of the alkene employed.

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