Catalytic aminohalogenation reaction of β-nitrostyrenes with N,N-dichloro-p-toluenesulfonamide resulting in dichlorinated haloamides with opposite regiochemistry to previous systems

Sanjun Zhi, Jianlin Han, Chen Lin, Guanghui An, Yi Pan, Guigen Li

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

Reaction of β-nitrostyrenes with N,N-dichloro-p-toluenesulfonamide (TsNCl2) has been successfully conducted by using either copper(I) chloride or 4-dimethylaminopyridine (DMAP) as the catalyst. The reaction resulted in dichlorohaloamine products with the opposite regiochemistry to that previously observed. In the presence of DMAP, the reaction proceeded smoothly to completion within 24 hours at room temperature and gave good chemical yields (65-88%). The structure of one of the products was confirmed by X-ray crystal structure analysis. This reaction is proposed to occur through a new mechanism involving a chloronium intermediate.

Original languageEnglish
Article numberM09207SS
Pages (from-to)1570-1574
Number of pages5
JournalSynthesis
Issue number10
DOIs
StatePublished - May 19 2008

Keywords

  • 4-dimethylaminopyridine
  • Aminohalogenation
  • N,N-dichloro-p-toluenesulfonamide
  • β-nitrostyrenes

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