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Rhodium-Biphephos-Catalyzed Tandem Isomerization–Hydroformylation of Oleonitrile

Univ Rennes, CNRS, Institut des Sciences Chimiques de Rennes, UMR 6226, F-35000 Rennes, France
Arkema France, CRRA, BP 63, Rue Henri Moissan, F-69493 Pierre Bénite, France
Arkema France, 420 Rue d’Estienne d’Orves, F-92705 Colombes, France
Author to whom correspondence should be addressed.
Catalysts 2018, 8(1), 21;
Received: 27 December 2017 / Revised: 9 January 2018 / Accepted: 9 January 2018 / Published: 12 January 2018
PDF [1625 KB, uploaded 18 January 2018]


Tandem isomerization–hydroformylation of oleonitrile (an 18-carbon nitrile with a remote internal (9-)C=C bond) has been studied using Rh-bisphosphite catalyst systems, targeting formation of the linear aldehyde. The best compromise between regioselectivity (l/b = 58:42) and chemoselectivity (60%) was obtained at 120 °C and 10 bar CO/H2 (1:1) with a catalyst based on Biphephos at a 0.5 mol % catalyst load and a low ligand excess (2 equiv. versus Rh). These values stand among the better reported ones for the tandem isomerization–hydroformylation of long chain olefins with a single-component catalyst system. View Full-Text
Keywords: tandem reaction; hydroformylation; isomerization; rhodium; Biphephos; oleonitrile tandem reaction; hydroformylation; isomerization; rhodium; Biphephos; oleonitrile

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Le Goanvic, L.; Ternel, J.; Couturier, J.-L.; Dubois, J.-L.; Carpentier, J.-F. Rhodium-Biphephos-Catalyzed Tandem Isomerization–Hydroformylation of Oleonitrile. Catalysts 2018, 8, 21.

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