Tandem hydroformylation/isomerization/hydrogenation of bio-derived 1-arylbutadienes for the regioselective synthesis of branched aldehydes

G.M. Vieira (1) , A.V. Granato (1) , E.V. Gusevskaya (1) , E.N. dos Santos (1) , Pierre H. Dixneuf (2) , Cédric Fischmeister (2) , Christian Bruneau (2)

1 UFMG - Universidade Federal de Minas Gerais = Federal University of Minas Gerais [Belo Horizonte, Brazil]
2 ISCR - Institut des Sciences Chimiques de Rennes

The rhodium-catalyzed hydroformylation of 1-arylbutadienes derived from lignocellulosic bio-resources has been carried out in toluene and green solvents. In the presence of DPPE and XANTPHOS ligands, a regioselective Markovnikov Rh-H insertion takes place resulting in branched aldehydes in high selectivity, which contrasts with previous results obtained from aliphatic conjugated dienes. Depending on the nature of the diphosphine ligand, conjugated enals or saturated aldehydes are obtained in good to excellent selectivity. The later have a potential interest for fragrance industry, as they are homologous to commercial fragrance ingredients.

Mots clés: Fragrance; Tandem catalysis; Hydroformylation

Domaines: Chimie organique; Catalyse

G.M. Vieira, A.V. Granato, E.V. Gusevskaya, E.N. dos Santos, Pierre H. Dixneuf, et al.. Tandem hydroformylation/isomerization/hydrogenation of bio-derived 1-arylbutadienes for the regioselective synthesis of branched aldehydes. Applied Catalysis A : General, 2020, 598, pp.117583. ⟨10.1016/j.apcata.2020.117583⟩. ⟨hal-02569952⟩