Experimental and Theoretical Study on the Olefin Metathesis of Alkenyl Baylis−Hillman Adducts Using Second-Generation Grubbs Catalyst

2004 ◽  
Vol 6 (19) ◽  
pp. 3313-3316 ◽  
Author(s):  
Mi Jung Lee ◽  
Ka Young Lee ◽  
Jin Yong Lee ◽  
Jae Nyoung Kim
Keyword(s):  
Olefin Metathesis ◽  
Second Generation ◽  
Theoretical Study ◽  
Grubbs Catalyst

Olefin metathesis, p‐Cresol and the Second Generation Grubbs Catalyst:  Fitting the Pieces

2021 ◽  
Author(s):  
Marthinus Rudi Swart ◽  
Linette Twigge ◽  
Elizabeth Erasmus ◽  
Charlene Marais ◽  
Barend Christiaan Bezuidenhoudt
Keyword(s):  
Olefin Metathesis ◽  
Second Generation ◽  
Grubbs Catalyst

scholarly journals A comprehensive study of olefin metathesis catalyzed by Ru-based catalysts

2015 ◽  
Vol 11 ◽  
pp. 1767-1780 ◽  
Author(s):  
Albert Poater ◽  
Luigi Cavallo
Keyword(s):  
Dft Calculations ◽  
Olefin Metathesis ◽  
Second Generation ◽  
Phosphine Ligands ◽  
Grubbs Catalyst ◽  
Heterocyclic Ligand ◽  
Grubbs Catalysts ◽  
Wide Range ◽  
First And Second Generation ◽  
Comprehensive Study

During a Ru-catalyzed reaction of an olefin with an alkylidene moiety that leads to a metallacycle intermediate, the cis insertion of the olefin can occur from two different directions, namely side and bottom with respect to the phosphine or N-heterocyclic ligand (NHC), depending on the first or second generation Grubbs catalyst. Here, DFT calculations unravel to which extent the bottom coordination of olefins with respect is favored over the side coordination through screening a wide range of catalysts, including first and second generation Grubbs catalysts as well as the subsequent Hoveyda derivatives. The equilibrium between bottom and side coordination is influenced by sterics, electronics, and polarity of the solvent. The side attack is favored for sterically less demanding NHC and/or alkylidene ligands. Moreover the generation of a 14-electron species is also discussed, with either pyridine or phosphine ligands to dissociate.

Amine-Mediated Degradation in Olefin Metathesis Reactions that Employ the Second-Generation Grubbs Catalyst

ChemCatChem ◽  
2014 ◽  
Vol 6 (2) ◽  
pp. 459-463 ◽  
Author(s):  
Justin A. M. Lummiss ◽  
Benjamin J. Ireland ◽  
Jacob M. Sommers ◽  
Deryn E. Fogg
Keyword(s):  
Olefin Metathesis ◽  
Second Generation ◽  
Grubbs Catalyst ◽  
Metathesis Reactions

New pseudohalide ligands in Ru-catalyzed olefin metathesis — A robust, air-activated iminopyrrolato catalyst

2005 ◽  
Vol 83 (6-7) ◽  
pp. 748-754 ◽  
Author(s):  
Samantha D Drouin ◽  
Heather M Foucault ◽  
Glenn PA Yap ◽  
Deryn E Fogg
Keyword(s):  
Key Words ◽  
Olefin Metathesis ◽  
High Reactivity ◽  
Ring Closing Metathesis ◽  
Grubbs Catalyst ◽  
X Ray ◽  
X Ray Crystallography

Reaction of the Grubbs catalyst RuCl2(PCy3)2(CHPh) (1) with lithium 2-[(2,6-diisopropylphenyl)imino]pyrrolide·Et2O (LiNN′·Et2O) gives alkylidene complex 5, containing a chelating, σ-bound iminopyrrolato unit. The structure of 5 is confirmed by X-ray crystallography. Treatment of 5 with pyridine generates RuCl(NN′)(py)2(CHPh) (6) via displacement of PCy3. Complex 5 effects ring-closing metathesis in air, displaying high reactivity relative to 6.Key words: ruthenium, alkylidene, metathesis, pyrrolimine, iminopyrrolato.

Second generation of Casiopeinas®: A joint experimental and theoretical study

2021 ◽  
Vol 517 ◽  
pp. 120201
Author(s):  
Miguel Reina ◽  
Luis Felipe Hernández-Ayala ◽  
María Elena Bravo-Gómez ◽  
Virginia Gómez ◽  
Lena Ruiz-Azuara
Keyword(s):  
Second Generation ◽  
Theoretical Study

Hoveyda–Grubbs catalyst confined in the nanocages of SBA-1: enhanced recyclability for olefin metathesis

2010 ◽  
Vol 46 (45) ◽  
pp. 8659 ◽  
Author(s):  
Hengquan Yang ◽  
Zhancheng Ma ◽  
Yuekui Wang ◽  
Yunwei Wang ◽  
Li Fang
Keyword(s):  
Olefin Metathesis ◽  
Grubbs Catalyst

ChemInform Abstract: Hoveyda-Grubbs′ Catalyst Confined in the Nanocages of SBA-1: Enhanced Recyclability for Olefin Metathesis.

ChemInform ◽  
2011 ◽  
Vol 42 (12) ◽  
pp. no-no
Author(s):  
Hengquan Yang ◽  
Zhancheng Ma ◽  
Yuekui Wang ◽  
Yunwei Wang ◽  
Li Fang
Keyword(s):  
Olefin Metathesis ◽  
Grubbs Catalyst

On the ligand properties of the P- versus the N-heterocyclic carbene for a Grubbs catalyst in olefin metathesis

2005 ◽  
Vol 690 (24-25) ◽  
pp. 6079-6088 ◽  
Author(s):  
Wolfgang W. Schoeller ◽  
Daniela Schroeder ◽  
A.B. Rozhenko
Keyword(s):  
Olefin Metathesis ◽  
Grubbs Catalyst

Quest for the ideal olefin metathesis catalyst

2008 ◽  
Vol 80 (1) ◽  
pp. 31-43 ◽  
Author(s):  
Anna Michrowska ◽  
Karol Grela
Keyword(s):  
Oxygen Atom ◽  
Quaternary Ammonium ◽  
Olefin Metathesis ◽  
Amino Group ◽  
Sulfonated Polystyrene ◽  
Grubbs Catalyst ◽  
Metathesis Catalyst ◽  
Metathesis Catalysts ◽  
Novel Strategy ◽  
The Ideal

Attempts were made to create a catalyst that approaches Gladysz's vision of an "ideal catalyst". Modifications of the Hoveyda-Grubbs catalyst were carried out with the aim to increase its activity and broaden the scope of its applicability to challenging metathesis reactions. This was done by introduction of an electron-withdrawing substituent on the isopropoxybenzylidene group in order to diminish the donor properties of the oxygen atom. The resulting stable and easily accessible nitro-substituted Hoveyda-Grubbs catalyst has found a number of successful applications in various research and industrial laboratories. Also, a new concept for noncovalent immobilization of a ruthenium olefin metathesis catalyst is presented. The 2-isopropoxybenzylidene ligand of Hoveyda-Grubbs carbene is further modified by an additional amino group, and immobilization is achieved by treatment with sulfonated polystyrene, forming the corresponding ammonium salt. In this novel strategy for the immobilization of ruthenium-based metathesis catalysts, the amino group plays a dual role, being first an active anchor for immobilization and secondly, after protonation, activating the catalysts by electron-donating to -withdrawing switch. The same concept has been used in the preparation of a quaternary ammonium catalyst for aqueous olefin metathesis.

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