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Catalytic Diamination of Alkenes using N , N ‐Dibromo‐ p ‐toluenesulfonamide as Electrophile and Nitriles as Nucleophiles
Author(s) -
Han Jianlin,
Li Tengfei,
Pan Yi,
Kattuboina Adiseshu,
Li Guigen
Publication year - 2008
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2007.00604.x
Subject(s) - nucleophile , chemistry , electrophile , catalysis , medicinal chemistry , organic chemistry , combinatorial chemistry
An efficient diamination reaction of alkenes has been developed for the synthesis of bromoalkyl‐branched imidazolines by using CuI–PPh 3 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 SnCl 4 as the promoter.