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The first total syntheses of sarcophytonolide H and the originally proposed and correct structures of isosarcophytonolide D have been achieved via transannular ring-closing metathesis (RCM). These total syntheses culminated in the stereostructural confirmation of sarcophytonolide H and the reassignment of isosarcophytonolide D, respectively. The antifouling activity of the synthetic sarcophytonolide H and its analogues was also evaluated.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Two complex norditerpenoids, caribenols A and B, were accessed from a common building block. Our synthesis of caribenol A features the diastereoselective formation of the seven-membered ring through a Friedel-Crafts triflation and a late-stage oxidation of a furan ring. The first synthesis of caribenol B was achieved using an intramolecular organocatalytic alpha-arylation. An unusual intramolecular aldol addition was developed for the assembly of its cyclopentenone moiety, and the challenging trans-diol moiety was installed through a selective nucleophilic addition to a hydroxy 1,2-diketone. Our overall synthetic strategy, which also resulted in a second-generation synthesis of amphilectolide, confirms the usefulness of furans as powerful nucleophiles and versatile synthons.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Discovery of (1,3-Dimesitylimidazolidin-2-ylidene)(2-isopropoxybenzylidene)ruthenium(VI) chloride

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In our search for more-selective olefin metathesis catalysts, a series of Hoveyda-Grubbs-type second-generation complexes bearing unsymmetrical N-heterocyclic carbene (NHC) ligands were synthesized and tested in model reactions. It was found that the N-benzyl substituent in NHC has a positive influence on the selectivity of the newly obtained catalysts in the self-metathesis reaction of alpha-olefins. As expected, a typical relationship between activity and selectivity with respect to the N-aryl substituent used was observed. Dipp-containing complexes exhibited higher stability at elevated temperature, while Mes-bearing complexes typically gave better yields than their Dipp analogues.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Discovery of (1,3-Dimesitylimidazolidin-2-ylidene)(2-isopropoxybenzylidene)ruthenium(VI) chloride

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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, together with density functional theory calculations (DFT), are presented. The complex is air- and moisture-stable, although has weak catalytical activity in the model metathesis reactions. However, its activity increases upon the addition of an aqueous HCl 1 M solution. Activated Ru complex successfully promotes metathesis in organic solvents as well as in water, enabling efficient performance (even up to 100%) of the catalyst under environment-friendly conditions. The activation mechanism of the reported catalyst is supported by time-dependent DFT calculations and ab initio molecular dynamics simulations.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Discovery of (1,3-Dimesitylimidazolidin-2-ylidene)(2-isopropoxybenzylidene)ruthenium(VI) chloride

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The build/couple/pair strategy has yielded small molecules with stereochemical and skeletal diversity by using short reaction sequences. Subsequent screening has shown that these compounds can achieve biological tasks considered challenging if not impossible (‘undruggable’) for small molecules. We have developed gold(I)-catalyzed cascade reactions of easily prepared propargyl propiolates as a means to achieve effective intermolecular coupling reactions for this strategy. Sequential alkyne activationof propargyl propiolates by a cationic gold(I) catalyst yields an oxoca rbenium ion that we previously showed is trapped by C-based nucleophilesat an extrannular site to yield alpha-pyrones. Here, we report O-base d nucleophiles react by ring opening to afford a novel polyfunctional product. In addition, by coupling suitable building blocks, we subsequently performed intramolecular pairing reactions that yield diverse and complex skeletons. These pairing reactions include one based on a novel aza-Wittig-6?-electrocyclization sequence and others based on ring-closing metathesis reactions.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Exquisite control of catalytic metathesis reactivity is possible through ligand-based variation of ruthenium carbene complexes. Sterically hindered alkenes, however, remain a generally recalcitrant class of substrates for intermolecular cross-metathesis. Allylic chalcogenides (sulfides and selenides) have emerged as ?privileged? substrates that exhibit enhanced turnover rates with the commercially available second-generation ruthenium catalyst. Increased turnover rates are advantageous when competing catalyst degradation is limiting, although specific mechanisms have not been defined. Herein, we describe facile cross-metathesis of allylic sulfone reagents with sterically hindered isoprenoid alkene substrates. Furthermore, we demonstrate the first example of intermolecular cross-metathesis of ruthenium carbenes with a tetrasubstituted alkene. Computational analysis by combined coupled cluster/DFT calculations exposes a favorable energetic profile for metallacyclobutane formation from chelating ruthenium beta-chalcogenide carbene intermediates. These results establish allylic sulfones as privileged reagents for a substrate-based strategy of cross-metathesis derivatization.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Awesome and Easy Science Experiments about (1,3-Dimesitylimidazolidin-2-ylidene)(2-isopropoxybenzylidene)ruthenium(VI) chloride

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The facile synthesis of two new unsymmetrical N-heterocyclic carbene (NHC) ligands from commercially available monosubstituted diamines is presented. The resultant unsymmetrical NHC ligands have been complexed to ruthenium to give novel olefin metathesis initiators. Of particular interest, the new complexes (7a and 8a) gave significantly different E:Z ratios in cross-metathesis reactions and gave an improved selectivity in diastereoselective ring-closing metathesis, in comparison to the corresponding Grubbs 2 (2) and Hoveyda – Grubbs (3) complexes.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

Top Picks: new discover of (1,3-Dimesitylimidazolidin-2-ylidene)(2-isopropoxybenzylidene)ruthenium(VI) chloride

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New pyridinium-tagged ruthenium catalysts have been synthesised to perform olefin metathesis in several media including both organic and aqueous solvents and room temperature ionic liquids (RTILs). High activity was obtained in the ring-closing metathesis (RCM) of a variety of di- or tri-substituted and/or oxygen-containing dienes. However, only fair levels of recycling combined with low to moderate residual ruthenium levels (25-173 ppm) have been observed showing clearly the difficulty of associating high activity and recyclability.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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A long-standing question in olefin metathesis centers on whether the “release-return” (boomerang) mechanism contributes to the productivity of Hoveyda-class catalysts. According to this mechanism, a molecule of o-isopropoxystyrene (A) is liberated during catalyst initiation, but recaptures the active catalyst following metathesis. The relevance of this pathway for the second-generation Hoveyda catalyst HII was assessed in metathesis of 1,1-and 1,2-disubstituted olefins. Crossover studies with 13C-labeled A*, as well as competition experiments involving ring-closing or cross metathesis (RCM, CM) in the presence of A (equimolar with HII) indicated rapid reuptake of styrenyl ether. The crossover studies indicated highly efficient catalyst initiation, with the entire catalyst charge being activated before metathesis was complete. In a comparative study involving CM of anethole with methyl acrylate, sustained activity was shown for HII, whereas the second-generation Grubbs catalyst GII was rapidly deactivated. These data demonstrate that the release-return mechanism is indeed operative for HII in these demanding metathesis reactions, and that facile shuttling from a protected recapture cycle into the productive metathesis cycle contributes to the superior performance of HII relative to GII.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI

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Efficient cross-metathesis of divinylsilanes and divinyldisiloxanes, carrying different electron-withdrawing substituents at silicon, with selected olefins in the presence of the first and second generation Grubbs catalyst and Hoveyda-Grubbs catalyst is described. The reaction was proved to be a valuable method for synthesis of unsaturated organosilicon derivatives and a model for the study of synthesis of oligo- and polymeric products via ADMET copolymerization of divinylsubstituted silanes and disiloxanes with dienes.

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Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI