Highly Efficient Ethenolysis and Propenolysis of Methyl Oleate Catalyzed by Abnormal N‑Heterocyclic Carbene Ruthenium Complexes in Combination with a Phosphine–Copper Cocatalyst

Fluorinated imidazo­[1,5-a]­pyridine abnormal carbene ruthenium complexes (F-aImPy–Ru) with a tricyclohexylphosphine copper chloride (Cy3P–CuCl) cocatalyst were developed for the ethenolysis/propenolysis of methyl oleate. These catalysts showed remarkable catalytic efficiencies (turnover numbers of...

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Published in:ACS catalysis 2020-09, Vol.10 (18), p.10592-10601
Main Authors: Byun, Seunghwan, Park, Seungwook, Choi, Youngseo, Ryu, Ji Yeon, Lee, Junseong, Choi, Jun-Ho, Hong, Sukwon
Format: Article
Language:English
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Summary:Fluorinated imidazo­[1,5-a]­pyridine abnormal carbene ruthenium complexes (F-aImPy–Ru) with a tricyclohexylphosphine copper chloride (Cy3P–CuCl) cocatalyst were developed for the ethenolysis/propenolysis of methyl oleate. These catalysts showed remarkable catalytic efficiencies (turnover numbers of 100,000 for ethenolysis and 200,000 for propenolysis) and excellent α-olefin selectivity (up to 99%). A computational study indicated that the energy barrier of the β-hydride elimination pathway in the presence of a phosphine–copper cocatalyst is higher than that in the absence of the cocatalyst, which might contribute to the improved longevity of the ruthenium catalyst in the reaction.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.0c02018