CuCl-catalyzed regio- and stereoselective aminohalogenation of α,β-unsaturated nitriles

Jian Lin Han, San Jun Zhi, Le Yong Wang, Yi Pan, Guigen Li

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63 Scopus citations

Abstract

α,β-Unsat1urated nitriles were found to be suitable substrates for aminochlorination with N,N-dichloro-p-toluenesulfonamide (4-TsNCl 2) in the presence of CuCl as the catalyst (10 mol-%) and 4 Å molecular sieves. The reaction is very convenient to carry out at room temperature without the protection of inert gases, and this method provides an easy route to vicinal haloamino nitriles with excellent regio- and stereoselectivities and in good chemical yields. The stereochemistry has been unambiguously confirmed by X-ray structural analysis.

Original languageEnglish
Pages (from-to)1332-1337
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number8
DOIs
StatePublished - 2007

Keywords

  • Aminohalogenation
  • Copper chloride
  • α,β-Unsaturated nitriles

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