Mitsunobu synthesis of symmetrical alkyl and polyfluoroalkyl secondary amines

Research output: Contribution to journalArticle

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 2005

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ether
Ether
Amines
Ethers
ethers
amines
1-Propanol
organic liquids
Heptane
Propanol
synthesis
heptanes
Amides
partition coefficient
boiling
Boiling liquids
amides
alcohol
partitions
alcohols

Keywords

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

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics

Cite this

Mitsunobu synthesis of symmetrical alkyl and polyfluoroalkyl secondary amines. / Bálint, Ana Maria; Bodor, A.; Gömöry, A.; Vékey, K.; Szabó, D.; Rábai, J.

In: Journal of Fluorine Chemistry, Vol. 126, No. 11-12, 12.2005, p. 1524-1530.

Research output: Contribution to journalArticle

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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.",
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author = "B{\'a}lint, {Ana Maria} and A. Bodor and A. G{\"o}m{\"o}ry and K. V{\'e}key and D. Szab{\'o} and J. R{\'a}bai",
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T1 - Mitsunobu synthesis of symmetrical alkyl and polyfluoroalkyl secondary amines

AU - Bálint, Ana Maria

AU - Bodor, A.

AU - Gömöry, A.

AU - Vékey, K.

AU - Szabó, D.

AU - Rábai, J.

PY - 2005/12

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N2 - 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.

AB - 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.

KW - Amines

KW - Fluorophilicity

KW - Ideal separation

KW - Mitsunobu reaction

KW - Trifluoromethanesulfonamide

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