Catalytic diamination of alkenes using N,N-dibromo-p-toluenesulfonamide as electrophile and nitriles as nucleophiles

Jianlin Han, Tengfei Li, Yi Pan, Adiseshu Kattuboina, Guigen Li

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28 Scopus citations

Abstract

An efficient diamination reaction of alkenes has been developed for the synthesis of bromoalkyl-branched imidazolines by using CuI-PPh3 as the catalyst and N,N-dibromo-p-toluenesulfonamide as the nitrogen/halogen sources. A good scope of alkene substrates, including α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins, was achieved for this reaction. Meanwhile, various nitriles were utilized as nucleophilic nitrogen sources. Modest to good yields and excellent regio- and stereoselectivity have been obtained. The stereochemistry was unambiguously confirmed by X-ray structural analysis. A new mild condition was found for the opening of resulting imidazolines by using SnCl4 as the promoter.

Original languageEnglish
Pages (from-to)71-77
Number of pages7
JournalChemical Biology and Drug Design
Volume71
Issue number1
DOIs
StatePublished - Jan 2008

Keywords

  • Copper iodide
  • Diamination
  • Imidazoline
  • N,N-dibromo-p-toluenesulfonamide
  • Tin tetrachloride

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