Mitsunobu synthesis of symmetrical alkyl and polyfluoroalkyl secondary amines

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19 Citations (Scopus)

Abstract

Trifluoromethanesulfonamides (triflamides) having the structure CF 3SO2N[(CH2)3R]2 (R = CnF2n + 1 or CnH2n + 1, n = 4, 6, 8, 10) are obtained in high yields, when CF3SO2NH 2 is reacted with 3-perfluoroalkyl-1-propanols or the parent aliphatic alcohols in a Mitsunobu reaction (Ph3P/[i-PrO 2CNNCO2-i-Pr]/ether). Products are isolated easily by fluorous extraction, fluorous solid-organic liquid filtration or n-heptane/CH3OH extraction. Consecutive deprotection of triflamides with LiAlH4 in boiling ether or dioxane solution affords the title amines in good overall yields. Fluorous partition coefficients of the F-tagged amides and amines are determined and qualitatively analyzed.

Original languageEnglish
Pages (from-to)1524-1530
Number of pages7
JournalJournal of Fluorine Chemistry
Volume126
Issue number11-12
DOIs
Publication statusPublished - Dec 1 2005

Keywords

  • Amines
  • Fluorophilicity
  • Ideal separation
  • Mitsunobu reaction
  • Trifluoromethanesulfonamide

ASJC Scopus subject areas

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

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