The combination of TsNH2 and NCS as nitrogen and chlorine sources for direct diamination of enones

Cody Timmons, Dianjun Chen, Xin Xu, Guigen Li

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

The regio-, stereo-, and chemoselective diamination of enones has been achieved without the observation of any haloamines. The reaction employs the readily available inexpensive combination of NCS and TsNH2 as an electrophilic nitrogen source, and three nitriles as nucleophilic nitrogen sources. A novel mechanism involving the formation of aziridinium intermediates from the reaction of TsNHCl with olefins and a new [2+3] cyclic addition for aziridinim ring opening has been proposed for the electrophilic diamination of olefins.

Original languageEnglish
Pages (from-to)3850-3854
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number19
DOIs
StatePublished - Sep 29 2003

Keywords

  • Aminations
  • Cycloadditions
  • Nitrogen heterocycles
  • Olefins

Fingerprint Dive into the research topics of 'The combination of TsNH<sub>2</sub> and NCS as nitrogen and chlorine sources for direct diamination of enones'. Together they form a unique fingerprint.

  • Cite this