Ionic liquid media resulted in more efficient regio- and stereoselective aminohalogenation of cinnamic esters

S. R.S.Saibabu Kotti, Xin Xu, Yining Wang, Allan D. Headley, Guigen Li

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

The ionic liquid, butylmethylimidazolium tetrafluoroborate ([Bmim][BF4]), was found to be superior to classical organic solvents for the metal catalyzed regio- and stereoselective aminohalogenation of cinnamic esters. The aminohalogenation reaction of cinnamic esters with p-TsNCl 2 proceeded at a faster rate (within 12 h) in the presence of a reduced amount of catalyst (CuOTf, 6.0 mol %). Good yields (76-82%) and excellent regio- and stereoselectivity (one isomer) were achieved for eight examples.

Original languageEnglish
Pages (from-to)7209-7212
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number39
DOIs
StatePublished - Sep 20 2004

Keywords

  • Aminohalogenation
  • Cinnamates
  • Copper(I)triflate
  • Ionic liquid

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