Ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoro-methanesulfonyl) imide, resulted in the first catalyst-free aminohalogenation of electron-deficient alkenes

Yi Ning Wang, Bukuo Ni, Allan D. Headley, Guigen Li

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

The 2-Ns-based aminohalogenation of α,β-unsaturated ketones has been achieved in an ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide {[bmim][N(SO2CF3) 2]}. [Bmim][N(SO2CF3)2] was found to be superior not only to classical organic solvents but also to its counterpart, [bmim][BF4], which was proven to be successful in the TsNCl 2-based aminohalogenation but failed to give any product for this reaction. The present process takes the advantage of 2-NsNCl2 as the stable nitrogen/halogen source in a one-pot operation without the use of any metal catalysts, it is convenient to perform without special protection of inert gases. Eight examples were examined with good to excellent stereoselectivity (1:5 to one isomer) and modest to good chemical yields (53-72%).

Original languageEnglish
Pages (from-to)319-322
Number of pages4
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number3
DOIs
StatePublished - Feb 2007

Keywords

  • Aminohalogenation
  • Haloamines
  • Ionic liquids
  • α,β-unsaturated ketones

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