Alkene Transfer Hydrogenation with Alkaline-Earth Metal Catalysts
Heiko Bauer1, Katharina Thum1, Mercedes Alonso2
1Chair of Inorganic and Organometallic Chemistry, Universität Erlangen-Nürnberg, Egerlandstrasse 1, 91058, Erlangen, Germany.
Abstract:
The alkene transfer hydrogenation (TH) of a variety of alkenes has been achieved with simple AeN''2 catalysts [Ae=Ca, Sr, Ba; N''=N(SiMe3 )2 ] using 1,4-cyclohexadiene (1,4-CHD) as a H source. Reaction of 1,4-CHD with AeN''2 gave benzene, N''H, and the metal hydride species N''AeH (or aggregates thereof), which is a catalyst for alkene hydrogenation. BaN''2 is by far the most active catalyst. Hydrogenation of activated C=C bonds (e.g. styrene) proceeded at room temperature without polymer formation. Unactivated (isolated) C=C bonds (e.g. 1-hexene) needed a higher temperature (120 °C) but proceeded without double-bond isomerization. The ligands fully control the course of the catalytic reaction, which can be: 1) alkene TH, 2) 1,4-CHD dehydrogenation, or 3) alkene polymerization. DFT calculations support formation of a metal hydride species by deprotonation of 1,4-CHD followed by H transfer. Convenient access to larger quantities of BaN''2 , its high activity and selectivity, and the many advantages of TH make this a simple but attractive procedure for alkene hydrogenation.
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