Design of bis-NHC Ru-complexes featuring diarylmethylene N-substituents for olefin metathesis

Idriss Curbet 1 Jennifer Morvan 1 Sophie Colombel-Rouen 1 Thierry Roisnel 1 Christophe Crévisy 1 Marc Mauduita 1
1 ISCR - Institut des Sciences Chimiques de Rennes
Abstract : New ruthenium indenylidene complexes containing N-heterocyclic carbene (NHC) ligands were synthesized and evaluated in olefin metathesis. The presence of two symmetrical saturated NHCs featuring N-diarylmethylene fragments (R= H, OMe or F) led to robust ruthenium precatalysts with a good latency. A kinetic study was investigated showing that a thermal stimulus (>60 degrees C) is required to reach an efficient catalytic initiation. Interestingly, a slight electronic effect was observed depending on the presence of an electron-donating or -withdrawing group within the diarylmethylene moiety. These complexes showed good activity at 1 mol% of catalyst loading in selected ring-closing metathesis (RCM) and cross-metathesis (CM) transformations. [GRAPHICS] .
Keywords : Olefin metathesis catalyst ruthenium NHC diaminocarbenes 1 3-dialkylimidazolinium salts
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Journal articles
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-02303421
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Submitted on : Wednesday, October 2, 2019 - 11:57:48 AM
Last modification on : Tuesday, November 12, 2019 - 4:58:32 PM

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ISCR | UNIV-RENNES1 | SCR-CD | CNRS | UR1-UFR-SPM | INC-CNRS | UNIV-RENNES | INSA-GROUPE

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Idriss Curbet, Jennifer Morvan, Sophie Colombel-Rouen, Thierry Roisnel, Christophe Crévisy, et al.. Design of bis-NHC Ru-complexes featuring diarylmethylene N-substituents for olefin metathesis. ARKIVOC - Online Journal of Organic Chemistry, Arkat USA Inc, 2019, 2019 (4), pp.102-112. ⟨10.24820/ark.5550190.p010.894⟩. ⟨hal-02303421⟩

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