Practice of fluorous biphase chemistry: Convenient synthesis of novel fluorophilic ethers via a Mitsunobu reaction

József Rábai, Dénes Szabó, Eszter K. Borbás, István Kövesi, István Kövesdi, Antal Csámpai, Ágnes Gömöry, Valeriy E. Pashinnik, Yuriy G. Shermolovich

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

The evolution of the term fluorous is addressed first, then a concise terminology is proposed, including fluorous partition coefficient, specific fluorophilicity and fluorousness. Some examples are shown for the design of higher generation fluorophilic molecules, involving Class I to Class III ponytails. Fluorophilic ethers of the structure of in high yields, when 2-aryl-1,1,1,3,3,3-hexafluoro-propanols are reacted either with trifluoroethyl- and 1H,1H-perfluorooctyl triflates (NaH/DMF, Williamson ether synthesis) or with 3-perfluorooctyl-propanol (Ph3P/EtO2CN=NCO2Et/PhCF3, Mitsunobu reaction), respectively. Fluorophilic phenol- and perfluoro-tert-butyl ethers can also be prepared effectively by the latter method. In case of higher homologues (n - 7,8) product isolation can be facilitated using fluorous extraction (C6F14/CH3OH). Specific fluorophilicity values of target molecules are estimated using a 2D method and compared with experimentally determined ones.

Original languageEnglish
Pages (from-to)199-207
Number of pages9
JournalJournal of Fluorine Chemistry
Volume114
Issue number2
DOIs
Publication statusPublished - May 8 2002

Keywords

  • Fluorine
  • Mitsunobu reaction
  • Perfluoroalkylmethyl triflates
  • Specific fluorophilicity

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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