Ruthenium-based complexes containing a benzimidazolium tag covalently connected to N-heterocyclic carbene ligands: environmentally friendly catalysts for olefin metathesis transformations

2013 ◽  
Vol 42 (20) ◽  
pp. 7354 ◽  
Author(s):  
Marek Klučiar ◽  
Karol Grela ◽  
Marc Mauduit
Keyword(s):  
Olefin Metathesis ◽  
Environmentally Friendly ◽  
Carbene Ligands

A succinct access to ω-hydroxylated jasmonates via olefin metathesis

2017 ◽  
Vol 72 (7-8) ◽  
pp. 285-292 ◽  
Author(s):  
Guillermo H. Jimenez-Aleman ◽  
Selina Seçinti ◽  
Wilhelm Boland
Keyword(s):  
Abiotic Stress ◽  
Olefin Metathesis ◽  
Higher Plants ◽  
Environmentally Friendly ◽  
Signaling Molecules ◽  
Synthetic Route ◽  
Limited Availability ◽  
Cross Metathesis ◽  
Physiological Processes

AbstractIn higher plants, jasmonates are lipid-derived signaling molecules that control many physiological processes, including responses to abiotic stress, defenses against insects and pathogens, and development. Among jasmonates, ω-oxidized compounds form an important subfamily. The biological roles of these ω-modified derivatives are not fully understood, largely due to their limited availability. Herein, a brief (two-step), simple and efficient (>80% yield), versatile, gram-scalable, and environmentally friendly synthetic route to ω-oxidized jasmonates is described. The approach utilizes olefin cross-metathesis as the key step employing inexpensive, commercially available substrates and catalysts.

scholarly journals Sterically Tuned N-Heterocyclic Carbene Ligands for the Efficient Formation of Hindered Products in Ru-Catalyzed Olefin Metathesis

ACS Catalysis ◽  
2020 ◽  
Vol 10 (19) ◽  
pp. 11394-11404
Author(s):  
Sebastian Planer ◽  
Paweł Małecki ◽  
Bartosz Trzaskowski ◽  
Anna Kajetanowicz ◽  
Karol Grela
Keyword(s):  
Olefin Metathesis ◽  
Carbene Ligands

scholarly journals Recent Advances in the Application of Ring-Closing Metathesis for the Synthesis of Unsaturated Nitrogen Heterocycles

Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1100-1114 ◽  
Author(s):  
Emilia Groso ◽  
Corinna Schindler
Keyword(s):  
Olefin Metathesis ◽  
Nitrogen Heterocycles ◽  
Short Review ◽  
Catalyst Design ◽  
Carbene Ligands ◽  
Ring Closing Metathesis ◽  
Recent Advances ◽  
Metathesis Reactions

This short review summarizes recent advances relating to the application of ring-closing olefin-olefin and carbonyl-olefin metathesis reactions towards the synthesis of unsaturated five- and six-membered nitrogen heterocycles. These developments include catalyst modifications and reaction designs that will enable access to more complex nitrogen heterocycles.1 Introduction2 Expansion of Ring-Closing Metathesis Methods3 Evaluation of Catalyst Design4 Indenylidene Catalysts5 Unsymmetrical N-Heterocyclic Carbene Ligands6 Carbonyl-Olefin Metathesis7 Conclusions

Ruthenium Catalysts Supported by Amino-Substituted N-Heterocyclic Carbene Ligands for Olefin Metathesis of Challenging Substrates

2017 ◽  
Vol 23 (8) ◽  
pp. 1950-1955 ◽  
Author(s):  
Vincent César ◽  
Yin Zhang ◽  
Wioletta Kośnik ◽  
Adam Zieliński ◽  
Adam A. Rajkiewicz ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Ruthenium Catalysts ◽  
Carbene Ligands

scholarly journals Consequences of the electronic tuning of latent ruthenium-based olefin metathesis catalysts on their reactivity

2015 ◽  
Vol 11 ◽  
pp. 1458-1468 ◽  
Author(s):  
Karolina Żukowska ◽  
Eva Pump ◽  
Aleksandra E Pazio ◽  
Krzysztof Woźniak ◽  
Luigi Cavallo ◽  
...  
Keyword(s):  
High Temperatures ◽  
Olefin Metathesis ◽  
Minor Amount ◽  
Carbene Ligands ◽  
Enhanced Activity ◽  
Electronic Tuning ◽  
Metathesis Catalysts ◽  
A Minor ◽  
Factor Governing

Two ruthenium olefin metathesis initiators featuring electronically modified quinoline-based chelating carbene ligands are introduced. Their reactivity in RCM and ROMP reactions was tested and the results were compared to those obtained with the parent unsubstituted compound. The studied complexes are very stable at high temperatures up to 140 °C. The placement of an electron-withdrawing functionality translates into an enhanced activity in RCM. While electronically modified precatalysts, which exist predominantly in the trans-dichloro configuration, gave mostly the RCM and a minor amount of the cycloisomerization product, the unmodified congener, which preferentially exists as its cis-dichloro isomer, shows a switched reactivity. The position of the equilibrium between the cis- and the trans-dichloro species was found to be the crucial factor governing the reactivity of the complexes.

From Environmentally Friendly Reusable Ionic-Tagged Ruthenium-Based Complexes to Industrially Relevant Homogeneous Catalysts: Toward a Sustainable Olefin Metathesis

Synlett ◽  
2017 ◽  
Vol 28 (07) ◽  
pp. 773-798 ◽  
Author(s):  
Marc Mauduit ◽  
Thibault Schmid ◽  
Adrien Dumas ◽  
Sophie Colombel-Rouen ◽  
Christophe Crévisy ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Environmentally Friendly ◽  
Homogeneous Catalysts

An attempt to provide an environmentally friendly solvent selection guide for olefin metathesis

2014 ◽  
Vol 16 (3) ◽  
pp. 1125-1130 ◽  
Author(s):  
Krzysztof Skowerski ◽  
Jacek Białecki ◽  
Andrzej Tracz ◽  
Tomasz K. Olszewski
Keyword(s):  
Olefin Metathesis ◽  
Environmentally Friendly ◽  
Solvent Selection

scholarly journals Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

2019 ◽  
Vol 15 ◽  
pp. 160-166 ◽  
Author(s):  
Łukasz Gułajski ◽  
Andrzej Tracz ◽  
Katarzyna Urbaniak ◽  
Stefan J Czarnocki ◽  
Michał Bieniek ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Microwave Irradiation ◽  
Ultrasonic Irradiation ◽  
Olefin Metathesis ◽  
Aqueous Media ◽  
Environmentally Friendly ◽  
Counter Ion

The influence of microwave and ultrasonic irradiation on the performance of ammonium-tagged Ru-based catalysts in olefin metathesis transformations in aqueous media was studied. Differences in the catalytic activity in correlation with the nature of the present counter ion and the size of the N-heterocyclic carbene (NHC) ligand were revealed. The presented methodology allows for preparation of a variety of polar and non-polar metathesis products under environmentally friendly conditions.

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