Alkene Transfer Hydrogenation with Alkaline-Earth Metal Catalysts

Bauer H, Thum K, Alonso M, Fischer C, Harder S (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Book Volume: 58

Pages Range: 4248-4253

Journal Issue: 13

DOI: 10.1002/anie.201813910

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, NH, and the metal hydride species NAeH (or aggregates thereof), which is a catalyst for alkene hydrogenation. BaN2 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 degrees 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 BaN2, its high activity and selectivity, and the many advantages of TH make this a simple but attractive procedure for alkene hydrogenation.

Authors with CRIS profile

Involved external institutions

Vrije Universiteit Brussel (VUB) Belgium (BE)

How to cite

APA:

Bauer, H., Thum, K., Alonso, M., Fischer, C., & Harder, S. (2019). Alkene Transfer Hydrogenation with Alkaline-Earth Metal Catalysts. Angewandte Chemie International Edition, 58(13), 4248-4253. https://dx.doi.org/10.1002/anie.201813910

MLA:

Bauer, Heiko, et al. "Alkene Transfer Hydrogenation with Alkaline-Earth Metal Catalysts." Angewandte Chemie International Edition 58.13 (2019): 4248-4253.

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