Potassium carbonate catalyzed regioselective aminohalogenation of β-nitrostyrenes by using benzyl carbamate/N-chlorosuccinimide as a new nitrogen/chlorine source

Xiaoyun Ji, Haibo Mei, Yu Qian, Jianlin Han, Guigen Li, Yi Pan

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

A combination of benzyl carbamate and N-chlorosuccinimide was developed as a new system for aminohalogenation of β-nitrostyrenes catalyzed by potassium carbonate in dichloromethane at room temperature. The reaction tolerates a wide range of substituents on the β-nitrostyrene, and proceeds smoothly in good-to-excellent chemical yields (77-99%). The new system shows a high efficiency and it markedly shortens the reaction time for aminochlorination. N,N-Dichlorobenzyl carbamate was also found to be a highly efficient source of both nitrogen and chlorine for the aminohalogenation reaction.

Original languageEnglish
Article numberH74711SS
Pages (from-to)3680-3686
Number of pages7
JournalSynthesis
Issue number22
DOIs
StatePublished - 2011

Keywords

  • alkenes
  • amides
  • aminations
  • carbamates
  • chlorinations

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