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

scholarly journals Olefin metathesis in nano-sized systems

2011 ◽  
Vol 7 ◽  
pp. 94-103 ◽  
Author(s):  
Didier Astruc ◽  
Abdou K Diallo ◽  
Sylvain Gatard ◽  
Liyuan Liang ◽  
Cátia Ornelas ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Covalent Attachment ◽  
Enyne Metathesis ◽  
Ring Closing Metathesis ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
Nano Catalysts

The interplay between olefin metathesis and dendrimers and other nano systems is addressed in this mini review mostly based on the authors’ own contributions over the last decade. Two subjects are presented and discussed: (i) The catalysis of olefin metathesis by dendritic nano-catalysts via either covalent attachment (ROMP) or, more usefully, dendrimer encapsulation – ring closing metathesis (RCM), cross metathesis (CM), enyne metathesis reactions (EYM) – for reactions in water without a co-solvent and (ii) construction and functionalization of dendrimers by CM reactions.

scholarly journals Low Catalyst Loadings in Olefin Metathesis: Synthesis of Nitrogen Heterocycles by Ring-Closing Metathesis

2010 ◽  
Vol 12 (5) ◽  
pp. 984-987 ◽  
Author(s):  
Kevin M. Kuhn ◽  
Timothy M. Champagne ◽  
Soon Hyeok Hong ◽  
Wen-Hao Wei ◽  
Andrew Nickel ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Nitrogen Heterocycles ◽  
Ring Closing Metathesis

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.

scholarly journals Catalytic, Transannular Carbonyl-Olefin Metathesis Reactions

2019 ◽  
Author(s):  
Paul Riehl ◽  
Daniel Nasrallah ◽  
Corinna Schindler
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Catalyst Design ◽  
Lewis Acid Catalysts ◽  
Complex Molecules ◽  
New Class ◽  
Metathesis Reactions ◽  
Lewis Acid Catalyst

A new class of Lewis acid-catalyzed carbonyl-olefin metathesis reactions is described that complements existing protocols for related ring-closing, ring-opening, and intermolecular transformations. These transannular carbonyl-olefin metathesis reactions rely on FeCl<sub>3</sub> as an inexpensive Lewis acid catalyst and are mechanistically distinct from previously developed protocols for ring closing, ring-opening and intermolecular metathesis. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction paths are competing to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to differentiate between these pathways to enable the selective formation of transannular carbonyl-ene or carbonyl-olefin metathesis products thus providing a valuable approach to the molecular editing of naturally occurring complex molecules. Additionally, these results are expected to enable further advances in catalyst design for carbonyl-olefin metathesis to ultimately develop efficient and high-yielding catalytic carbonyl olefination reactions.

Olefin Metathesis as an Inorganic Synthetic Tool:  Cross and Ring Closing Metathesis Reactions of Diruthenium-Bound ω-Alkene-α-carboxylates

2007 ◽  
Vol 46 (9) ◽  
pp. 3775-3782 ◽  
Author(s):  
Wei-Zhong Chen ◽  
John D. Protasiewicz ◽  
Stephen A. Davis ◽  
James B. Updegraff ◽  
Li-Qing Ma ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Ring Closing Metathesis ◽  
Metathesis Reactions

A simple and practical preparation of an efficient water soluble olefin metathesis catalyst

2015 ◽  
Vol 17 (6) ◽  
pp. 3407-3414 ◽  
Author(s):  
Zhen J. Wang ◽  
W. Roy Jackson ◽  
Andrea J. Robinson
Keyword(s):  
Olefin Metathesis ◽  
Water Soluble ◽  
Ring Closing Metathesis ◽  
Cross Metathesis ◽  
Metathesis Catalyst ◽  
Metathesis Reactions ◽  
Scale Preparation

A facile gram-scale preparation of a di-ammonium functionalised Ru-alkylidene complex which efficiently catalyses ring-closing metathesis and cross-metathesis reactions in water.

scholarly journals The Influence of Various N-Heterocyclic Carbene Ligands on Activity of Nitro-Activated Olefin Metathesis Catalysts

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2282 ◽  
Author(s):  
Michał Pieczykolan ◽  
Justyna Czaban-Jóźwiak ◽  
Maura Malinska ◽  
Krzysztof Woźniak ◽  
Reto Dorta ◽  
...  
Keyword(s):  
High Activity ◽  
Olefin Metathesis ◽  
Double Bonds ◽  
Carbene Ligands ◽  
Grubbs Catalyst ◽  
Metathesis Reactions ◽  
Metathesis Catalysts

A set of nitro-activated ruthenium-based Hoveyda-Grubbs type olefin metathesis catalysts bearing sterically modified N-hetero-cyclic carbene (NHC) ligands have been obtained, characterised and studied in a set of model metathesis reactions. It was found that catalysts bearing standard SIMes and SIPr ligands (4a and 4b) gave the best results in metathesis of substrates with more accessible C–C double bonds. At the same time, catalysts bearing engineered naphthyl-substituted NHC ligands (4d–e) exhibited high activity towards formation of tetrasubstituted C–C double bonds, the reaction which was traditionally Achilles’ heel of the nitro-activated Hoveyda–Grubbs catalyst.

scholarly journals Catalytic, Transannular Carbonyl-Olefin Metathesis Reactions

2019 ◽  
Author(s):  
Paul Riehl ◽  
Daniel Nasrallah ◽  
Corinna Schindler
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Ring Opening ◽  
Acid Catalyst ◽  
Catalyst Design ◽  
Lewis Acid Catalysts ◽  
Complex Molecules ◽  
New Class ◽  
Metathesis Reactions ◽  
Lewis Acid Catalyst

A new class of Lewis acid-catalyzed carbonyl-olefin metathesis reactions is described that complements existing protocols for related ring-closing, ring-opening, and intermolecular transformations. These transannular carbonyl-olefin metathesis reactions rely on FeCl<sub>3</sub> as an inexpensive Lewis acid catalyst and are mechanistically distinct from previously developed protocols for ring closing, ring-opening and intermolecular metathesis. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction paths are competing to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to differentiate between these pathways to enable the selective formation of transannular carbonyl-ene or carbonyl-olefin metathesis products thus providing a valuable approach to the molecular editing of naturally occurring complex molecules. Additionally, these results are expected to enable further advances in catalyst design for carbonyl-olefin metathesis to ultimately develop efficient and high-yielding catalytic carbonyl olefination reactions.

ChemInform Abstract: Low Catalyst Loadings in Olefin Metathesis: Synthesis of Nitrogen Heterocycles by Ring-Closing Metathesis: Synthesis of Nitrogen Heterocycles by Ring-Closing Metathesis.

ChemInform ◽  
2010 ◽  
Vol 41 (29) ◽  
pp. no-no
Author(s):  
Kevin M. Kuhn ◽  
Timothy M. Champagne ◽  
Soon Hyeok Hong ◽  
Wen-Hao Wei ◽  
Andrew Nickel ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Nitrogen Heterocycles ◽  
Ring Closing Metathesis

Ruthenium Complexes Bearing Two N-Heterocyclic Carbene Ligands in Low Catalyst Loading Olefin Metathesis Reactions

2010 ◽  
Vol 29 (13) ◽  
pp. 3007-3011 ◽  
Author(s):  
Xavier Bantreil ◽  
Rebecca A. M. Randall ◽  
Alexandra M. Z. Slawin ◽  
Steven P. Nolan
Keyword(s):  
Olefin Metathesis ◽  
Ruthenium Complexes ◽  
Catalyst Loading ◽  
Carbene Ligands ◽  
Metathesis Reactions ◽  
Low Catalyst Loading
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