The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides

Sanjun Zhi, Haibo Mei, Guangqian Zhang, Hao Sun, Jianlin Han, Guigen Li, Yi Pan

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The combination of benzamide and NCS was found to be an efficient nitrogen/halogen source for aminohalogenation of β-nitrostyrenes. The reaction was convenient to carry out by using 4-dimethylaminopyridine as the catalyst, resulting in vicinal dichlorinated haloamino nitroalkanes with opposite regiochemistry to that generated from other electron-deficient olefins observed previously. The reaction proceeded smoothly at room temperature with good yields and excellent regioselectivities. A mechanism involving a chloronium intermediate was proposed to explain the resulting regiochemistry. The current system explored a new type of nitrogen sources for aminohalogenation of functionalized olefins.

Original languageEnglish
Pages (from-to)1946-1952
Number of pages7
JournalScience China Chemistry
Volume53
Issue number9
DOIs
StatePublished - Sep 2010

Keywords

  • DMAP
  • aminohalogenation
  • benzamide
  • haloamides
  • β-nitrostyrenes

Fingerprint Dive into the research topics of 'The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides'. Together they form a unique fingerprint.

Cite this