A versatile and highly Z -Selective olefin metathesis ruthenium catalyst based on a readily accessible N -heterocyclic carbene

Abstract : A ruthenium catalyst for Z-selective olefin metathesis has been synthesized from a readily accessible N-heterocyclic carbene (NHC) ligand that is prepared using an efficient, practical, and scalable multicomponent synthesis. The desired ruthenium complex with cyclometalated NHC ligand is obtained by means of selective C(sp3)-H activation at the adamantyl fragment and X-ray diffraction analysis unambiguously confirmed the structure of the precatalyst. The catalyst demonstrated attractive catalytic performance in self- and cross-metathesis at low catalyst loading to afford the desired internal olefins with high conversion and very high Z-selectivity (up to andgt;99%). The versatility of the chelated catalyst is illustrated by the high cis-selectivity (up to andgt;98%) and high tacticity control (up to andgt;98% syndiotactic) achieved in ring-opening polymerization, allowing for the production of highly microstructurally controlled norbornene-, norbornadiene-, and cyclopropene-derived polymers.
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A. Dumas, R. Tarrieu, T. Vives, T. Roisnel, V. Dorcet, et al.. A versatile and highly Z -Selective olefin metathesis ruthenium catalyst based on a readily accessible N -heterocyclic carbene. ACS Catalysis, American Chemical Society, 2018, 8 (4), pp.3257-3262. ⟨10.1021/acscatal.8b00151⟩. ⟨hal-01774411⟩

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