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.

Graphical abstractTreatment 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 full-size imageDownload 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.