Rhenium-catalyzed insertion of terminal alkenes into a C(sp2)–H bond and successive transfer hydrogenation

Treatment of aromatic aldimines with terminal alkenes in the presence of a rhenium catalyst, [HRe(CO)4]n, gives 2-alkenylbenzylamines in good to excellent yields. This reaction proceeds via the insertion of the alkene into a C–H bond at the ortho-position of the imino group of the aromatic aldimine followed by sequential β-hydride elimination from the formed alkyl rhenium intermediate and then by hydrogenation of the imino group of the aldimine.

Treatment of aromatic aldimines with terminal alkenes in the presence of a rhenium catalyst, [HRe(CO)4]n, gives 2-alkenylbenzylamines in good to excellent yields. This reaction proceeds via the insertion of the alkene into a C–H bond followed by sequential β-hydride elimination and hydrogenation.Figure optionsDownload as PowerPoint slideResearch highlights
► A rhenium complex, [HRe(CO)4]n, catalyzes the synthesis of 2-alkenylbenzylamines.
► 2-Alkenylbenzylamines are produced from aromatic aldimines and alkenes.
► A quinoline derivative is provided in the case of using [ReBr(CO)3(thf)]2.