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Gawron, Martin; Gilch, Franziska; Schmidhuber, Daniel; Kelly, John A.; Horsley Downie, Thomas M.; Jacobi von Wangelin, Axel; Rehbein, Julia; Wolf, Robert
Angewandte Chemie, February 5, 2024, Letnik: 63, Številka: 6Journal Article
We show that countercations exert a remarkable influence on the ability of anionic cobaltate salts to catalyze challenging alkene hydrogenations. An evaluation of the catalytic properties of CatCo(η4‐cod)2 (Cat=K (1), Na (2), Li (3), (Depnacnac)Mg (4), and N(nBu)4 (5); cod=1,5‐cyclooctadiene, Depnacnac={2,6‐Et2C6H3NC(CH3)}2CH)) demonstrated that the lithium salt 3 and magnesium salt 4 drastically outperform the other catalysts. Complex 4 was the most active catalyst, which readily promotes the hydrogenation of highly congested alkenes under mild conditions. A plausible catalytic mechanism is proposed based on density functional theory (DFT) investigations. Furthermore, combined molecular dynamics (MD) simulation and DFT studies were used to examine the turnover‐limiting migratory insertion step. The results of these studies suggest an active co‐catalytic role of the counterion in the hydrogenation reaction through the coordination to cobalt hydride intermediates. The counterion makes a difference in alkene hydrogenations promoted by low‐valence cobaltate salts. The best performing catalyst cleanly hydrogenated various alkenes (including tri‐ and tetra‐substituted) under mild conditions. Mechanistic studies point toward a homotopic catalyst and show how counterion coordination to hydride intermediates modulates the barrier for the turnover‐limiting migratory insertion.
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