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

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...

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Published inARKIVOC free online journal of organic chemistry Vol. 2019; no. 4; pp. 102 - 112
Main Authors Curbet, Idriss, Morvan, Jennifer, Colombel-Rouen, Sophie, Roisnel, Thierry, Crévisy, Christophe, Mauduit, Marc
Format Journal Article
LanguageEnglish
Published Arkat USA Inc 01.01.2019
Arkat USA, Inc
Subjects
Chemical Sciences
1
ruthenium
diaminocarbenes
catalyst
NHC
3-dialkylimidazolinium salts
Olefin metathesis
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Summary: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] .
ISSN:1551-7012
1551-7004
1551-7012
DOI:10.24820/ark.5550190.p010.894