scholarly journals Recent advances in ruthenium-based olefin metathesis

2018 ◽  
Vol 47 (12) ◽  
pp. 4510-4544 ◽  
Author(s):  
O. M. Ogba ◽  
N. C. Warner ◽  
D. J. O’Leary ◽  
R. H. Grubbs
Keyword(s):  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Functional Group ◽  
Polymer Science ◽  
Enabling Technology ◽  
Broad Applicability ◽  
Recent Advances ◽  
Metathesis Catalysts

Ruthenium-based olefin metathesis catalysts, known for their functional group tolerance and broad applicability in organic synthesis and polymer science, continue to evolve as an enabling technology in these areas.

Ligand-Driven Advances in Iridium Catalyzed sp3 C-H Borylation: 2,2’-Dipyridylarylmethane

Synlett ◽  
2020 ◽  
Author(s):  
Margaret R Jones ◽  
Nathan D. Schley
Keyword(s):  
Recent Work ◽  
Organic Synthesis ◽  
Functional Group ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Additional Ligand ◽  
Limited Application ◽  
Hydrocarbon Substrates ◽  
Phenanthroline Ligands

The field of catalytic C-H borylation has grown considerably since its founding, providing a means for the preparation of synthetically versatile organoborane products. While sp2 C-H borylation methods have found widespread and practical use in organic synthesis, the analogous sp3 C-H borylation reaction remains challenging and has seen limited application. Existing catalysts are often hindered by incomplete consumption of the diboron reagent, poor functional group tolerance, harsh reaction conditions, and the need for excess or neat substrate. These challenges acutely affect C-H borylation chemistry of unactivated hydrocarbon substrates, which has lagged in comparison to methods for the C-H borylation of activated compounds. Herein we discuss recent advances in sp3 C-H borylation of undirected substrates in the context of two particular challenges: (1) utilization of the diboron reagent and (2) the need for excess or neat substrate. Our recent work on the application of dipyridylarylmethane ligands in sp3 C-H borylation has allowed us to make contributions in this space and has presented an additional ligand scaffold to supplement traditional phenanthroline ligands.

scholarly journals Olefin metathesis in air

2015 ◽  
Vol 11 ◽  
pp. 2038-2056 ◽  
Author(s):  
Lorenzo Piola ◽  
Fady Nahra ◽  
Steven P Nolan
Keyword(s):  
Transition Metal ◽  
Olefin Metathesis ◽  
Functional Group ◽  
High Oxidation State ◽  
Catalytic Systems ◽  
Metal Centers ◽  
Early Transition Metal ◽  
Significant Interest ◽  
High Oxidation ◽  
Metathesis Catalysts

Since the discovery and now widespread use of olefin metathesis, the evolution of metathesis catalysts towards air stability has become an area of significant interest. In this fascinating area of study, beginning with early systems making use of high oxidation state early transition metal centers that required strict exclusion of water and air, advances have been made to render catalysts more stable and yet more functional group tolerant. This review summarizes the major developments concerning catalytic systems directed towards water and air tolerance.

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.

Recent advances in olefin metathesis and its application in organic synthesis

Tetrahedron ◽  
1998 ◽  
Vol 54 (18) ◽  
pp. 4413-4450 ◽  
Author(s):  
Robert H. Grubbs ◽  
Sukbok Chang
Keyword(s):  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Recent Advances

Biocatalysis for Sustainable Organic Synthesis

2004 ◽  
Vol 57 (4) ◽  
pp. 281 ◽  
Author(s):  
Roger A. Sheldon ◽  
Fred van Rantwijk
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Solvent System ◽  
Fine Chemicals ◽  
Reaction Conditions ◽  
Organic Syntheses ◽  
Recent Advances ◽  
Cascade Processes

Biocatalysis offers mild reaction conditions, an environmentally attractive catalyst–solvent system, high activities, and chemo-, regio-, and stereoselectivities, while the use of enzymes generally circumvents the need for functional group activation and avoids protection/deprotection steps required in traditional organic syntheses. This review, using β-lactam antibiotics as an example, discusses recent advances in biocatalysis research towards the goal of ‘green’ methodologies for the manufacture of (fine) chemicals and the emulation of a cell's enzymatic cascade processes.

scholarly journals Stable CAAC-based Ruthenium Complexes for Dynamic Olefin Metathesis Under Mild Conditions

2021 ◽  
Author(s):  
Oleksandr Kravchenko ◽  
Brian J.J. Timmer ◽  
Maurice Biedermann ◽  
Andrew Kentaro Inge ◽  
Olof Ramstrom
Keyword(s):  
Olefin Metathesis ◽  
High Stability ◽  
Room Temperature ◽  
Functional Group ◽  
Biologically Active ◽  
Dynamic Covalent Chemistry ◽  
Mild Conditions ◽  
Cross Metathesis ◽  
Potential Applications ◽  
Metathesis Catalysts

<p>A series of olefin metathesis catalysts bearing cyclic (alkyl)(amino)carbene (CAAC) ligands of varying size and steric demand has been synthesized and evaluated in ring-closing-, self-, and cross-metathesis reactions at room temperature. The catalysts were also probed for potential applications in dynamic covalent chemistry. The majority of the catalysts showed high stability, and remained active in the reaction mixtures for several days, including in methanol-based solutions. Higher temperatures could be used to control the reactivity towards sterically challenging substrates, enabling formation of tetrasubstituted olefins. The CAAC complexes exhibited remarkable functional group tolerance towards heteroaromatic and nucleophilic additives, making them potentially useful in the screening of biologically active compounds.</p>

ChemInform Abstract: Recent Advances of Olefin Metathesis and It′s Applications in Organic Synthesis

ChemInform ◽  
2012 ◽  
Vol 43 (26) ◽  
pp. no-no ◽  
Author(s):  
P. Naresh ◽  
M. Sirisha ◽  
K. Vijay ◽  
N. Srinath
Keyword(s):  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Recent Advances

scholarly journals Stable CAAC-based Ruthenium Complexes for Dynamic Olefin Metathesis Under Mild Conditions

2021 ◽  
Author(s):  
Oleksandr Kravchenko ◽  
Brian J.J. Timmer ◽  
Maurice Biedermann ◽  
Andrew Kentaro Inge ◽  
Olof Ramstrom
Keyword(s):  
Olefin Metathesis ◽  
High Stability ◽  
Room Temperature ◽  
Functional Group ◽  
Biologically Active ◽  
Dynamic Covalent Chemistry ◽  
Mild Conditions ◽  
Cross Metathesis ◽  
Potential Applications ◽  
Metathesis Catalysts

<p>A series of olefin metathesis catalysts bearing cyclic (alkyl)(amino)carbene (CAAC) ligands of varying size and steric demand has been synthesized and evaluated in ring-closing-, self-, and cross-metathesis reactions at room temperature. The catalysts were also probed for potential applications in dynamic covalent chemistry. The majority of the catalysts showed high stability, and remained active in the reaction mixtures for several days, including in methanol-based solutions. Higher temperatures could be used to control the reactivity towards sterically challenging substrates, enabling formation of tetrasubstituted olefins. The CAAC complexes exhibited remarkable functional group tolerance towards heteroaromatic and nucleophilic additives, making them potentially useful in the screening of biologically active compounds.</p>

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