A mild and efficient rhenium-catalyzed transfer hydrogenation of terminal olefins using alcoholysis of amine–borane adducts as a reducing system

[ReBr2(NO)(CH3CN)(PTA)2] (PTA = 1, 3, 5-triaza-7-phosphaadamantane) catalyzes the alcoholysis of ammonia–borane and amine–boranes and the catalytic transfer hydrogenations of various terminal olefins. Excellent yields were achieved at 70 °C in isopropanol using tBuOK as a co-catalyst affording TOF values up to 396 h−1.

Alcoholysis of various ammonia–borane and amine–boranes and catalytic transfer hydrogenation of the terminal olefins have been developed. tBuOK was introduced as a co-catalyst for the reaction system. A possible reaction mechanism for the alcoholysis and the transfer hydrogenation is presented.Figure optionsDownload as PowerPoint slideHighlights
► Alcoholysis of various ammonia-borane and amine-boranes have been developed.
► Catalytic transfer hydrogenations of the terminal olefins have been developed.
► tBuOK was introduced as a co-catalyst for the reaction system.
► A possible mechanism for the alcoholysis and the transfer hydrogenation is presented.