Olefin Metathesis: Catalyst Development, Microwave Catalysis, and Domino Applications

2005 ◽  
Vol 58 (1) ◽  
pp. 3 ◽  
Author(s):  
Steven G. Aitken ◽  
Andrew D. Abell
Keyword(s):  
Olefin Metathesis ◽  
Historical Development ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Catalyst Development ◽  
Metathesis Catalyst ◽  
Convenient Route ◽  
The Way

Olefin metathesis, a process by which alkylidene groups on alkenes are exchanged, is reviewed with reference to the historical development of functional catalysts and microwave catalysis. The advent of new catalysts and improved reaction conditions has paved the way for the development of new and versatile domino processes that combine either different metathesis events or a key metathesis reaction with another reaction in a particularly atom economic and ‘green’ sense. We review this area as a convenient route to some otherwise difficult to prepare systems.

scholarly journals Light-Activated Olefin Metathesis: Catalyst Development, Synthesis, and Applications

2020 ◽  
Vol 53 (10) ◽  
pp. 2456-2471
Author(s):  
Or Eivgi ◽  
Ravindra S. Phatake ◽  
Noy B. Nechmad ◽  
N. Gabriel Lemcoff
Keyword(s):  
Olefin Metathesis ◽  
Catalyst Development ◽  
Metathesis Catalyst

scholarly journals Iodonium-Catalyzed Carbonyl–Olefin Metathesis Reactions

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1966-1970 ◽  
Author(s):  
Giulia Oss ◽  
Thanh Vinh Nguyen
Keyword(s):  
Transition Metal ◽  
Organic Compounds ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Lewis Acids ◽  
Functional Group ◽  
Iodine Monochloride ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Recent Developments

The carbonyl–olefin metathesis reaction has become increasingly important in organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl–olefin metathesis process under mild reaction conditions. This work broadens the scope of this chemical transformation to include iodonium sources as simple and practical catalysts.

scholarly journals In tandem or alone: a remarkably selective transfer hydrogenation of alkenes catalyzed by ruthenium olefin metathesis catalysts

2015 ◽  
Vol 13 (9) ◽  
pp. 2684-2688 ◽  
Author(s):  
Grzegorz Krzysztof Zieliński ◽  
Cezary Samojłowicz ◽  
Tomasz Wdowik ◽  
Karol Grela
Keyword(s):  
Olefin Metathesis ◽  
Transfer Hydrogenation ◽  
Selective Transfer ◽  
Metathesis Reaction ◽  
Metathesis Catalyst ◽  
Selective System ◽  
Metathesis Catalysts

A remarkably selective system for transfer hydrogenation of alkenes, composed of Grubbs’ ruthenium metathesis catalyst and HCOONa/HCOOH, is presented. This system can also be formed directly after a metathesis reaction to effect hydrogenation in a single-pot.

Molecular Iodine-Catalyzed Carbonyl-Olefin Metathesis

2018 ◽  
Author(s):  
Thanh Vinh Nguyen ◽  
Uyen P. N. Tran ◽  
Giulia Oss ◽  
Martin Breugst ◽  
Eric Detmar ◽  
...  
Keyword(s):  
Chemical Transformation ◽  
Olefin Metathesis ◽  
Functional Group ◽  
Molecular Iodine ◽  
Mechanistic Studies ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Elemental Iodine

The carbonyl-olefin metathesis reaction is a synthetically valuable transformation that could facilitate rapid functional group interconversion and construction of new organic structures. Herein we demonstrate that elemental iodine, a very simple and mild catalyst, can efficiently promote this chemical transformation under mild reaction conditions with excellent outcomes. Our mechanistic studies revealed intriguing aspects of iodine activation mode that could change the previously established perception of catalyst and substrate design for the carbonyl-olefin metathesis reaction.

Enhancement of ruthenium-catalyzed olefin metathesis reactions: Searching for new catalyst or new reaction conditions?

2011 ◽  
Vol 83 (3) ◽  
pp. 553-563 ◽  
Author(s):  
Anna Szadkowska ◽  
Cezary Samojłowicz ◽  
Karol Grela
Keyword(s):  
Olefin Metathesis ◽  
Industrial Process ◽  
Catalyst Design ◽  
Chemical Transformations ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Efficient Tool ◽  
Complex Molecules ◽  
Unique Reaction ◽  
Selection Of

Olefin metathesis as a catalytic process constantly gains interest among organic chemists. Over the last decade, it became an efficient tool to accomplish the synthesis of many complex molecules. The development of new well-defined catalysts and continuous examination of novel ligands led to the establishment of metathesis methodology in a group of widespread chemical transformations. Not only does the selection of the catalyst seem to be of crucial importance, but modifying the reaction conditions, such as choice of the solvent and temperature, also allows one to make olefin metathesis a practical industrial process. This contribution, based on examples from our research, is devoted to answering the question “What may have a greater impact on the performance of metathesis reaction: a sophisticated catalyst design or unique reaction conditions?” Based on the data reported in the paper, we discuss two complementary strategies concerning the tuning of the olefin metathesis process.

Molecular Iodine-Catalyzed Carbonyl-Olefin Metathesis

2018 ◽  
Author(s):  
Thanh Vinh Nguyen ◽  
Uyen P. N. Tran ◽  
Giulia Oss ◽  
Martin Breugst ◽  
Eric Detmar ◽  
...  
Keyword(s):  
Chemical Transformation ◽  
Olefin Metathesis ◽  
Functional Group ◽  
Molecular Iodine ◽  
Mechanistic Studies ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Elemental Iodine

The carbonyl-olefin metathesis reaction is a synthetically valuable transformation that could facilitate rapid functional group interconversion and construction of new organic structures. Herein we demonstrate that elemental iodine, a very simple and mild catalyst, can efficiently promote this chemical transformation under mild reaction conditions with excellent outcomes. Our mechanistic studies revealed intriguing aspects of iodine activation mode that could change the previously established perception of catalyst and substrate design for the carbonyl-olefin metathesis reaction.

Connecting catalytic cycles by organometallic transformations in situ: Novel perspectives in the olefin metathesis field

2006 ◽  
Vol 78 (2) ◽  
pp. 469-476 ◽  
Author(s):  
Bernd Schmidt
Keyword(s):  
Double Bond ◽  
Olefin Metathesis ◽  
Metathesis Reaction ◽  
Ring Closing Metathesis ◽  
Double Bond Isomerization ◽  
Metathesis Catalyst ◽  
Organometallic Transformations ◽  
Catalytic Cycles

Tandem sequences consisting of an olefin metathesis step and a subsequent non-metathesis reaction become accessible by organometallic transformations of the Ru-carbene species in situ. This contribution highlights some tandem sequences that rely on the conversion of the metathesis catalyst to Ru-hydrides, with special emphasis on the tandem ring-closing metathesis (RCM)-double-bond isomerization sequence.

Synthesis of Pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by Alkyne-Carbonyl Metathesis

Synthesis ◽  
2020 ◽  
Author(s):  
Peter Ehlers ◽  
Peter Langer ◽  
Marian Blanco Ponce ◽  
Silvio Parpart ◽  
Alexander Villinger ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Metathesis Reaction ◽  
Synthetic Methodology ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Modular Synthesis

AbstractA concise and modular synthesis of pyrrolo[1,2-a][1,6]- and [1,8]naphthyridines by a one-pot two-step reaction consisting of electrophilic acylation followed by an alkyne-carbonyl-metathesis reaction as the final cyclization step is reported. This developed synthetic methodology allows the facile synthesis of these heterocyclic core structures in mainly high overall yields under metal-free conditions. Reaction conditions are carefully optimized and display a novel supplement to access these tricyclic heterocyclic compounds.

A Light-Activated Olefin Metathesis Catalyst Equipped with a Chromatic Orthogonal Self-Destruct Function

2015 ◽  
Vol 128 (2) ◽  
pp. 774-777 ◽  
Author(s):  
Revannath L. Sutar ◽  
Efrat Levin ◽  
Danielle Butilkov ◽  
Israel Goldberg ◽  
Ofer Reany ◽  
...  
Keyword(s):  
Olefin Metathesis ◽  
Metathesis Catalyst
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