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  • Title: Catalytic diamination of alkenes using N,N-dibromo-p-toluenesulfonamide as electrophile and nitriles as nucleophiles.
    Author: Han J, Li T, Pan Y, Kattuboina A, Li G.
    Journal: Chem Biol Drug Des; 2008 Jan; 71(1):71-7. PubMed ID: 18069987.
    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 alpha,beta-unsaturated ketones, alpha,beta-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.
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