Rhodium-Biphephos-Catalyzed Tandem Isomerization-Hydroformylation of Oleonitrile

Lucas Le Goanvic (1) , Jérémy Ternel (1) , Jean-Luc Couturier (2) , Jean-Luc Dubois (3) , Jean-François Carpentier (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 CRRA - Centre de recherche Rhône-Alpes
3 Arkema

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 degrees C and 10 bar CO/H-2 (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.

Keywords: tandem reaction; hydroformylation; isomerization; rhodium; Biphephos; oleonitrile

Domains: Chemical Sciences

Lucas Le Goanvic, Jérémy Ternel, Jean-Luc Couturier, Jean-Luc Dubois, Jean-François Carpentier. Rhodium-Biphephos-Catalyzed Tandem Isomerization-Hydroformylation of Oleonitrile. Catalysts, 2018, 8 (1), pp.21. ⟨10.3390/catal8010021⟩. ⟨hal-01709525⟩