Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide

Heterocyclic communications

article

Liansheng Wang¹  Yi Pan¹  Hongwen Hu¹ 

[1] School of Chemistry and Chemical Engineering, Nanjing University;School of Chemistry and Materials Science, Hubei Engineering University

关键词: alkylation;    cyclic cascade reactions;    dihydropyrrole;    Heck reaction;   

DOI  :  10.1515/hc-2012-0090

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

Reaction of N,N -diallyl- p -toluenesulfonamide 1 with benzyl halides 2 in the presence of a palladium catalyst afforded a series of novel dihydropyrroles 3 in moderate yields. A palladium-catalyzed self-cyclization reaction of the diene 1 may take place to give a cyclic dihydropyrrole 4 during the reaction. It is proposed that the cyclic products 4 are formed via a palladium-catalyzed cascade cyclization-coupling process. Reaction of phenyl iodide 5 with 1 in the same condition afforded normal Heck vinylation products 6 .

【 授权许可】

CC BY|CC BY-NC-ND