Highly selective macrocyclic ring-closing metathesis of terminal olefins in non-chlorinated solvents at low dilution

Adrien Dumas (1) , Sophie Colombel-Rouen (1) , Idriss Curbet (1) , Gwenael Forcher (1) , Fabien Tripoteau (2) , Frederic Caijo (2) , Pierre Queval (2) , Mathieu Rouen (2) , Olivier Baslé (1) , Marc Mauduit (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 DEMETA SAS

A set of new ruthenium-indenylidene complexes bearing two unsymmetrical unsaturated N-cycloalkyl-NHC ligands were synthesized. These catalysts proved to be highly selective in the macrocyclic ring-closing metathesis performed in non-chlorinated solvents at low dilution (0.01 M). Without the requirement of benzoquinone derivatives to prevent the isomerisation side reactions, this environmentally friendly catalytic process promoted the synthesis of macrocyclic odorant molecules with remarkable > 99% purity.

Domains: Chemical Sciences; Chemical Sciences; Catalysis

Adrien Dumas, Sophie Colombel-Rouen, Idriss Curbet, Gwenael Forcher, Fabien Tripoteau, et al.. Highly selective macrocyclic ring-closing metathesis of terminal olefins in non-chlorinated solvents at low dilution. Catalysis Science & Technology, 2019, 9 (2), pp.436-443. ⟨10.1039/c8cy02115e⟩. ⟨hal-02049520⟩