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• 1576-98-3 trans-1,4-diacetoxy-2-butene 
• 591-87-7 Allyl acetate 

Relevant academic research and scientific papers

Synthesis and Application of Stereoretentive Ruthenium Catalysts on the Basis of the M7 and the Ru-Benzylidene-Oxazinone Design

A series of new stereoretentive ruthenium catalysts bearing the dithiocatecholate ligand was synthesiszed on the basis of the M7 and Ru-benzylidene-oxazinone design. The activity of the catalysts was tested in ring-opening cross-metathesis reactions, ring

Ruthenabenzene: A Robust Precatalyst

Metallaaromatics constitute a unique class of aromatic compounds where one or more transition metal elements are incorporated into the aromatic system, the parent of which is metallabenzene. One of the main concerns about metallabenzenes generally deals with the structural characterization related to their relative aromaticity compared to the carbon archetype. Transition metal-containing metallabenzenes are also implicated in certain catalytic processes such as alkyne metathesis polymerization; however, these transition metal-based metallaaromatic compounds have not been developed as a catalyst. Herein, we describe an effective strategy to generate diverse arrays of ruthenabenzenes and demonstrated them as an aromatic equivalent of the Grubbs-type ruthenium alkylidene catalysts. These ruthenabenzenes can be prepared via an enyne metathesis and metallotropic [1,3]-shift cascade process to form alkyne-chelated ruthenium alkylidene intermediates followed by spontaneous cycloaromatization. The aromatic nature of these complexes was confirmed by spectroscopic and X-ray crystallographic data, and the mechanistic pathways for the cycloaromatization process were studied by DFT calculations. These ruthenabenzenes display robust catalytic activity for metathesis and other transformations, which illustrates that metallabenzenes are not only compounds of structural and theoretical interests but also are a novel platform for new catalyst development.

Activated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde

Two EWG-activated Hoveyda-Grubbs-type ruthenium complexes (Sil-II and Sil-II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a commercially available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests disclosed that the bulkier NHC-ligand bearing catalyst Sil-II’ is visibly more stable and productive than its smaller NHC-analogue Sil-II. Good application profile of catalyst Sil-II’ was confirmed in a set of diverse metathesis reactions including ring-closing metathesis (RCM) and cross-metathesis (CM) of complex polyfunctional substrates of medicinal chemistry interest, including a challenging macrocyclization of the Pacritinib precursor. Compatibility of the new catalyst with various green solvents was checked and metathesis of Sildenafil and Tadalafil-based substrates was successfully conducted in acetone. The mechanism of Sil-II’ initiation has been investigated through kinetic experiments unveiling that the decrease of the steric hindrance of the chelating alkoxy moiety (from iPrO to EtO) favors the interchange initiation pathway over the typical dissociation pathway for other popular 2nd generation Hoveyda-Grubbs catalysts. (Figure presented.).

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

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.

In a Quest for Selectivity Paired with Activity: A Ruthenium Olefin Metathesis Catalyst Bearing an Unsymmetrical Phenanthrene-Based N-Heterocyclic Carbene

Robust, selective, and stable in the presence of ethylene, ruthenium olefin metathesis pre-catalyst, {[3-benzyl-1-(10-phenyl-9-phenanthryl)]-2-imidazolidinylidene}dichloro(o-isopropoxyphenylmethylene)ruthenium(II), Ru-3, bearing an unsymetrical N-heterocyclic carbene (uNHC) ligand, has been synthesized. The initiation rate of Ru-3 was examined by ring-closing metathesis and cross-metathesis reactions with a broad spectrum of olefins, showing an unprecendented selectivity. It was also tested in industrially relevant ethenolysis reactions of olefinic substrates from renewable feedstock with very good yields and selectivities.

Compositions And Methods For Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis

The present disclosure provides compositions and methods for metathesizing a first alkenyl or alkynyl group with a second alkenyl or alkynyl group, the composition comprising a ruthenium metathesis catalyst and a photoredox catalyst that is activated by v

A Fluorescence-Based High-Throughput Screening Method for Olefin Metathesis Using a Ratiometric Fluorescent Probe

(Z)-1,8-Di(pyren-1-yl)oct-4-ene (1) was prepared as a probe for olefin metathesis. The conversions of substrate by olefin metathesis under various conditions were calculated using the ratiometric fluorescence intensity change of 1. The conversions calcula

Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis

Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis cat

New olefin metathesis catalyst bearing N-mesitylimidazole and nitrate ligands – Synthesis, activity, and performance in aqueous media

A new 18-electron ruthenium complex, where ruthenium catalytic center is coordinated with the N-mesitylimidazole and nitrate ligands, as well as o-isopropoxystyrene moiety, is reported. The synthesis and detailed characterization of the Ru complex, togeth

Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis

Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis cat