Z-Selective Cross Metathesis with Ruthenium Catalysts: Synthetic Applications and Mechanistic Implications

2015 ◽  
Vol 54 (17) ◽  
pp. 5018-5024 ◽  
Author(s):  
Myles B. Herbert ◽  
Robert H. Grubbs
Keyword(s):  
Ruthenium Catalysts ◽  
Cross Metathesis

Tandem Catalytic Acrylonitrile Cross-Metathesis and Hydrogenation of Nitriles with Ruthenium Catalysts: Direct Access to Linear α,ω-Aminoesters from Renewables

ChemSusChem ◽  
2012 ◽  
Vol 5 (8) ◽  
pp. 1410-1414 ◽  
Author(s):  
Xiaowei Miao ◽  
Cédric Fischmeister ◽  
Christian Bruneau ◽  
Pierre H. Dixneuf ◽  
Jean-Luc Dubois ◽  
...  
Keyword(s):  
Ruthenium Catalysts ◽  
Direct Access ◽  
Cross Metathesis ◽  
Hydrogenation Of Nitriles

Functionalization vs. degradation of 1,4-polybutadiene by ruthenium complex catalyzed reaction with vinylsilanes

2001 ◽  
Vol 79 (5-6) ◽  
pp. 775-779 ◽  
Author(s):  
Bogdan Marciniec ◽  
Ewa Malecka ◽  
Jacek Gulinski ◽  
Monika Grundwald-Wyspianska ◽  
Mariusz Lewandowski
Keyword(s):  
Ruthenium Complex ◽  
Ruthenium Complexes ◽  
Ruthenium Catalysts ◽  
Cross Metathesis ◽  
Higher Temperature ◽  
Partial Degradation

Polybutadiene (I) containing 91% of 1,4-(cis-trans) units and 9% of 1,2-units in the presence of vinyltriethoxysilane (II) and ruthenium catalysts RuCl2(PPh3)3 (III), RuHCl(CO)(PPh3)3 (IV), and [RuCl2(CO)3]2 (V) at 100-130°C undergoes functionalization and (or) partial degradation as an effect of competitive silylative coupling of =C-H and cross-metathesis of I with II. Significant degradation of I occurs at lower temperatures (100-110°C) (particularly when the process is carried out in air), but exclusive functionalization of I is observed at higher temperature (120-130°C) regardless of the atmosphere (air or argon) used.Key words: functionalization, degradation, polybutadiene, ruthenium complexes.

scholarly journals The cross-metathesis of methyl oleate with cis-2-butene-1,4-diyl diacetate and the influence of protecting groups

2011 ◽  
Vol 7 ◽  
pp. 1-8 ◽  
Author(s):  
Arno Behr ◽  
Jessica Pérez Gomes
Keyword(s):  
Methyl Oleate ◽  
Renewable Resources ◽  
Value Added ◽  
Ruthenium Catalysts ◽  
Protecting Groups ◽  
Catalyst Loading ◽  
Reaction Conditions ◽  
Functional Monomers ◽  
Cross Metathesis ◽  
The Cross

Background: α,ω-Difunctional substrates are useful intermediates for polymer synthesis. An attractive, sustainable and selective (but as yet unused) method in the chemical industry is the oleochemical cross-metathesis with preferably symmetric functionalised substrates. The current study explores the cross-metathesis of methyl oleate (1) with cis-2-butene-1,4-diyl diacetate (2) starting from renewable resources and quite inexpensive base chemicals. Results: This cross-metathesis reaction was carried out with several phosphine and N-heterocyclic carbene ruthenium catalysts. The reaction conditions were optimised for high conversions in combination with high cross-metathesis selectivity. The influence of protecting groups present in the substrates on the necessary catalyst loading was also investigated. Conclusions: The value-added methyl 11-acetoxyundec-9-enoate (3) and undec-2-enyl acetate (4) are accessed with nearly quantitative oleochemical conversions and high cross-metathesis selectivity under mild reaction conditions. These two cross-metathesis products can be potentially used as functional monomers for diverse sustainable polymers.

Highly Active Chiral Ruthenium Catalysts for Asymmetric Cross- and Ring-Opening Cross-Metathesis

2006 ◽  
Vol 118 (45) ◽  
pp. 7753-7757 ◽  
Author(s):  
Jacob M. Berlin ◽  
Steven D. Goldberg ◽  
Robert H. Grubbs
Keyword(s):  
Ring Opening ◽  
Ruthenium Catalysts ◽  
Cross Metathesis ◽  
Highly Active

Fluoro-imidazopyridinylidene Ruthenium Catalysts for Cross Metathesis with Ethylene

2019 ◽  
Vol 38 (21) ◽  
pp. 4121-4132 ◽  
Author(s):  
Seunghwan Byun ◽  
Huiyeong Seo ◽  
Jun-Ho Choi ◽  
Ji Yeon Ryu ◽  
Junseong Lee ◽  
...  
Keyword(s):  
Ruthenium Catalysts ◽  
Cross Metathesis

Efficient Z-Selective Olefin-Acrylamide Cross-Metathesis Enabled by Sterically Demanding Cyclometalated Ruthenium Catalysts

2020 ◽  
Vol 142 (50) ◽  
pp. 20987-20993
Author(s):  
Yan Xu ◽  
Jonathan J. Wong ◽  
Adrian E. Samkian ◽  
Jeong Hoon Ko ◽  
Shuming Chen ◽  
...  
Keyword(s):  
Ruthenium Catalysts ◽  
Cross Metathesis ◽  
Sterically Demanding

Highly Active Chiral Ruthenium Catalysts for Cross-Metathesis

Synfacts ◽  
2007 ◽  
Vol 2007 (2) ◽  
pp. 0185-0185 ◽  
Author(s):  
R. Grubbs ◽  
J. Berlin ◽  
S. Goldberg
Keyword(s):  
Ruthenium Catalysts ◽  
Cross Metathesis ◽  
Highly Active

Cross metathesis with acrylates: N ‐heterocyclic carbene (NHC)‐ versus cyclic alkyl amino carbene (CAAC)‐based ruthenium catalysts, an unanticipated influence of the carbene type on efficiency and selectivity of the reaction

ChemCatChem ◽  
2020 ◽  
Vol 12 (24) ◽  
pp. 6366-6374
Author(s):  
Katarzyna Kaczanowska ◽  
Bartosz Trzaskowski ◽  
Aleksandra Peszczyńska ◽  
Andrzej Tracz ◽  
Rafał Gawin ◽  
...  
Keyword(s):  
Ruthenium Catalysts ◽  
Cross Metathesis

Cross metathesis of methyl oleate (MO) with terminal, internal olefins by ruthenium catalysts: factors affecting the efficient MO conversion and the selectivity

RSC Advances ◽  
2016 ◽  
Vol 6 (103) ◽  
pp. 100925-100930 ◽  
Author(s):  
Nor Wahida Awang ◽  
Ken Tsutsumi ◽  
Barbora Huštáková ◽  
Siti Fairus M. Yusoff ◽  
Kotohiro Nomura ◽  
...  
Keyword(s):  
Methyl Oleate ◽  
High Selectivity ◽  
Ruthenium Catalysts ◽  
Factors Affecting ◽  
Cross Metathesis

Cross metathesis (CM) of methyl oleate (MO) with cis-4-octene, cis-stilbene, allyltrimethylsilane by RuCl2(PCy3)(IMesH2)(CHPh) yielded CM products with high MO conversion, high selectivity; the effect of olefin substituents, conditions was explored.

Highly Active Chiral Ruthenium Catalysts for Asymmetric Cross- and Ring-Opening Cross-Metathesis.

ChemInform ◽  
2007 ◽  
Vol 38 (12) ◽  
Author(s):  
Jacob M. Berlin ◽  
Steven D. Goldberg ◽  
Robert H. Grubbs
Keyword(s):  
Ring Opening ◽  
Ruthenium Catalysts ◽  
Cross Metathesis ◽  
Highly Active
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