Mixed Isobutylphobane/N‐Heterocyclic Carbene Ruthenium‐ Indenylidene Complexes: Synthesis and Catalytic Evaluation in Olefin Metathesis Reactions

Sauvage, Xavier; Zaragoza, Guillermo; Demonceau, Albert; Delaude, Lionel

doi:10.1002/adsc.201000207

Cited by 31 publications

(13 citation statements)

References 122 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ruthenium olefin metathesis catalysts are known to be unstable in the presence of ethylene. − However, if steps are undertaken to remove ethylene from the reaction mixture, long catalyst life times can be realized . We thus decided to investigate the cross-metathesis between alkyl crotonates and propylene (Scheme ) using the Hoveyda–Blechert catalyst (Figure ), , which proved to be one of the more active catalysts examined herein (vide infra).…”

Section: Resultsmentioning

confidence: 99%

Acrylates via Metathesis of Crotonates

Schweitzer

Snell

2014

Org. Process Res. Dev.

View full text Add to dashboard Cite

Crotonic acid has the potential to be produced from renewable resources at low cost but currently has a limited market. We are investigating catalytic routes to exploit the functionalities of crotonic acid to produce a range of established industrial chemicals. Here we report our work on converting crotonates to acrylates, where a cost-competitive bio-based alternative can provide a market advantage. Our optimized reaction conditions for the cross-metathesis between crotonates and ethylene resulted in an increase in catalyst turnover numbers by 2 orders of magnitude compared with literature values. Control experiments showed the cross-metathesis with ethylene to be an equilibrium reaction. The turnover-number-limiting factor was found to be the stability of the metathesis catalyst.

show abstract

Section: Resultsmentioning

confidence: 99%

Acrylates via Metathesis of Crotonates

Schweitzer

Snell

2014

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…Standard benchmark screening procedures, ROMP of COD and the RCM catalytic tests were performed as in literature. 21,30,37,38 Experimental details are given below.…”

mentioning

confidence: 99%

Synthesis and characterization of non-chelating ruthenium–indenylidene olefin metathesis catalysts derived from substituted 1,1-diphenyl-2-propyn-1-ols

Xie

Hamad

et al. 2015

New J. Chem.

View full text Add to dashboard Cite

show abstract

“…The catalytic study of complexes 4f – 4h in comparison with complex 4a was started with a ring‐closing metathesis (RCM) of the model substrate DEDAM (equation ) using a catalyst loading of 1 mol% at 38°C in CH 2 Cl 2. [11a,15] The kinetic profiles of the conversions are shown in Figure . In the figure, all complexes 4f – 4h and 4a exhibit similar performances and none exhibit better catalytic ability than the others in any stage of the profiles.…”

Section: Resultsmentioning

confidence: 99%

SIMes/PCy₃ mixed ligand‐coordinated alkyl group‐tagged ruthenium indenylidene complexes: Synthesis, characterization and metathesis activity

et al. 2018

Applied Organom Chemis

View full text Add to dashboard Cite

We report on the synthesis and characterization of SIMes/PCy 3 mixed ligandcoordinated second-generation ruthenium catalysts, bearing various 3-alkyl-1indenylidene ligands, denoted as RuCl 2 (3-alkyl-1-indenylidene)(SIMes)(PCy 3 ), in which alkyl is isopropyl (4f), tert-butyl (4g) or cyclohexyl (4h). The characterization of complexes 4f-4h was performed using infrared spectroscopy, elemental analysis, high-resolution mass spectrometry and NMR spectroscopy. In addition, the configuration of complexes 4f and 4g was analyzed using singlecrystal X-ray diffraction analysis. The catalytic activities of 4f-4h were evaluated in the olefin metathesis reaction of the ring-closing metathesis of diethyl diallylmalonate, and the ring-opening metathesis polymerization of cis,ciscyclooctadiene in comparison with the reference complex 4a. The results reveal that all complexes 4a and 4f-4h exhibit similar catalytic activity towards the tested substrates. Careful analysis of the catalyst performance and single-crystal X-ray diffraction data of the obtained complexes reveals that the steric modification on the 3-alkyl group shows a negligible influence on the ligand congestion around the ruthenium center as well as on the catalytic activities in the metathesis reactions.

show abstract

Mixed Isobutylphobane/N‐Heterocyclic Carbene Ruthenium‐ Indenylidene Complexes: Synthesis and Catalytic Evaluation in Olefin Metathesis Reactions

Cited by 31 publications

References 122 publications

Acrylates via Metathesis of Crotonates

Acrylates via Metathesis of Crotonates

Synthesis and characterization of non-chelating ruthenium–indenylidene olefin metathesis catalysts derived from substituted 1,1-diphenyl-2-propyn-1-ols

SIMes/PCy₃ mixed ligand‐coordinated alkyl group‐tagged ruthenium indenylidene complexes: Synthesis, characterization and metathesis activity

Contact Info

Product

Resources

About

Mixed Isobutylphobane/N‐Heterocyclic Carbene Ruthenium‐ Indenylidene Complexes: Synthesis and Catalytic Evaluation in Olefin Metathesis Reactions

Cited by 31 publications

References 122 publications

Acrylates via Metathesis of Crotonates

Acrylates via Metathesis of Crotonates

Synthesis and characterization of non-chelating ruthenium–indenylidene olefin metathesis catalysts derived from substituted 1,1-diphenyl-2-propyn-1-ols

SIMes/PCy3 mixed ligand‐coordinated alkyl group‐tagged ruthenium indenylidene complexes: Synthesis, characterization and metathesis activity

Contact Info

Product

Resources

About

SIMes/PCy₃ mixed ligand‐coordinated alkyl group‐tagged ruthenium indenylidene complexes: Synthesis, characterization and metathesis activity