Palladium(?)-Catalyzed Stereospecific Alkenyl C-H Bond Alkylation Of Allylamines

Direct transition metal-catalyzed C-H alkylation has become a popular and highly efficient method for C-C bond formation.Alkylation of aromatic C(sp2)-H and aliphatic C(sp3)-H is well documented,but direct functionalization of alkenyl C(sp2)-H remains relatively challenging due to competing reactions involving unsaturated ? bonds in alkenes which would lead numerous side reactions.A potentially attractive solution is stereospecific synthesis of substituted alkenes via directing group-mediated C(alkenyl)-H alkylation.This approach can generate synthetically useful stereospecific multi-substituted alkenes.Despite impressive progress in this field,success has been limited primarily to activated alkenes such as ?,?-unsaturated carbonyl compounds,vinylpyridines,?,?-unsaturated imines,enamides and enolates.In contrast,reactions with inactive alkenes remain largely undeveloped.We report the palladium-catalyzed,isoquinoline-1-carboxamide(IQA)-directed alkylation of allylamines with alkyl iodides.Isoquinoline-1-carboxamide(IQA)acts as directing group to generate multi-substituted olefim products in cis configuration in moderate to good yields.Mechanistic studies suggest that alkenyl C-H bond activation is the rate-determining step.