In Situ Generation of Ru-Based Metathesis Catalyst. A Systematic Study

Daniel S. Müller (1) , Yann Raoul (2) , Jerome Le Notre (3) , Olivier Baslé (1, 4) , Marc Mauduit (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 SAS OLEON
3 SAS PIVERT
4 LCC - Laboratoire de chimie de coordination

A systematic study for the in situ generation of Ru-based metathesis catalysts was described. Assembly of commercially available and inexpensive reagents [Ru(p-cymene)Cl-2](2), SIPr center dot HCl, and n-BuLi led to the formation of 18 electron arene-ruthenium complexes that, in the presence of additives such as alkynes, cyclopropenes, and diazoesters, generated highly selective and efficient catalytic systems applicable to a variety of olefin metathesis transformations. Notably, we were able to achieve a productive TON of 4500 for the self-metathesis of methyl oleate, a reaction which could be easily upscaled to 2 kg.

Mots clés: in situ; N-heterocyclic carbene ligand; Olefin metathesis; Ruthenium; Arene complexes; NHC ligand

Domaines: Chimie; Catalyse

Daniel S. Müller, Yann Raoul, Jerome Le Notre, Olivier Baslé, Marc Mauduit. In Situ Generation of Ru-Based Metathesis Catalyst. A Systematic Study. ACS Catalysis, 2019, 9 (4), pp.3511-3518. ⟨10.1021/acscatal.9b00244⟩. ⟨hal-02115712⟩