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.

scholarly journals Ru-based Z-selective metathesis catalysts with modified cyclometalated carbene ligands

2014 ◽  
Vol 5 (10) ◽  
pp. 4091-4098 ◽  
Author(s):  
Sarah M. Bronner ◽  
Myles B. Herbert ◽  
Paresma R. Patel ◽  
Vanessa M. Marx ◽  
Robert H. Grubbs
Keyword(s):  
Olefin Metathesis ◽  
Carbene Ligands ◽  
Metathesis Catalysts

A series of cyclometalated Z-selective ruthenium olefin metathesis catalysts with alterations to the N-heterocyclic carbene (NHC) ligand were prepared.

Ruthenium Olefin Metathesis Catalysts with N-Heterocyclic Carbene Ligands BearingN-Naphthyl Side Chains

2010 ◽  
Vol 29 (4) ◽  
pp. 775-788 ◽  
Author(s):  
Ludovic Vieille-Petit ◽  
Hervé Clavier ◽  
Anthony Linden ◽  
Sascha Blumentritt ◽  
Steven P. Nolan ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Side Chains ◽  
Carbene Ligands ◽  
Metathesis Catalysts

A thermally robust ruthenium phosphonium alkylidene catalyst — the effect of more bulky N-heterocyclic carbene ligands on catalyst performance in olefin metathesis reactions

2013 ◽  
Vol 91 (10) ◽  
pp. 935-942 ◽  
Author(s):  
Erin M. Leitao ◽  
Warren E. Piers ◽  
Masood Parvez
Keyword(s):  
Olefin Metathesis ◽  
Second Generation ◽  
The Other ◽  
Carbene Ligands ◽  
Thermal Stabilities ◽  
Excellent Activity ◽  
Metathesis Reactions ◽  
Test Reactions ◽  
Overall Efficiency ◽  
Alkylidene Complexes

Three new ruthenium phosphonium alkylidene complexes incorporating N-heterocyclic carbene ligands with bulky N-aryl groups (2,6-diethyl, L = 1,3-bis(2,6-diethylphenyl)imidazolin-2-ylidene (H2IDEP) and 2,6-diisopropyl, L = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (H2ID-i-PP)) were synthesized and characterized. The H2ID-i-PP supported complex was found to exhibit excellent thermal stabilities relative to the parent N-mesityl (N-Mes) complexes as well as the H2IDEP supported complexes. All three phosphonium alkylidenes were evaluated in comparison to the N-Mes derivative and Grubbs second generation catalyst using standard olefin metathesis reactions and conditions. The complex containing the bulky H2ID-i-PP ligand was found to have excellent activity and longevity in comparison to the other catalysts. Although initiation rates were slow for this sterically bulky precatalyst, its superior activity led to the best overall efficiency in test reactions.

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