Catalytic diamination of alkenes using N,N-dibromo-p-toluenesulfonamide as electrophile and nitriles as nucleophiles.
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.
Han
Jianlin
J
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, PR China.
Li
Tengfei
T
Pan
Yi
Y
Kattuboina
Adiseshu
A
Li
Guigen
G
D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D018360:Crystallography, X-Ray; D004583:Electrons; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000475:Alkenes; C527490:N,N-dibromo-p-toluenesulfonamide; D009570:Nitriles; D013449:Sulfonamides