Category: 258278-25-0

Das, Rajesh published the artcileStrategic design of a bifunctional Ag(I)-grafted NHC-MOF for efficient chemical fixation of CO₂ from a dilute gas under ambient conditions, Synthetic Route of 258278-25-0, the publication is Inorganic Chemistry Frontiers (2022), 9(11), 2583-2593, database is CAplus.

The chem. fixation of carbon dioxide into valuable products constitutes a promising step toward reducing the atm. CO₂ concentration Consequently, herein we report the strategic design of a bifunctional catalyst by grafting catalytically active Ag(I) ions onto N-heterocyclic carbene (NHC) sites in a MOF for efficient chem. fixation of CO₂ from a dilute gas to oxazolidinones, bio-relevant commodity chems. Indeed, Ag(I)@MOF-NHC demonstrated excellent catalytic activity for efficient fixation of CO₂ from a dilute gas (CO₂ : N₂ = 13 : 87%) with alkynes to afford valuable chems., oxazolidinones, under RT and atm. pressure (balloon) conditions. The superior activity of the Ag(I) anchored MOF over the individual (AgNO₃ and MOF-NHC) components has been ascribed to the synergistic effect between the CO₂-philic NHC and alkynophilic Ag(I) sites exposed in the 1D channels of the MOF. Furthermore, the Ag(I) anchored MOF showed high recyclability without significant loss of catalytic activity and structural rigidity. Overall, this is a unique demonstration of the utilization of dilute CO₂ under environmentally friendly mild conditions and can pave the way for the development of efficient catalytic systems for sustainable utilization of CO₂ from dilute gases.

Inorganic Chemistry Frontiers published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, Synthetic Route of 258278-25-0.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Scattolin, Thomas published the artcileIndenyl and Allyl Palladate Complexes Bearing N-Heterocyclic Carbene Ligands: an Easily Accessible Class of New Anticancer Drug Candidates, Synthetic Route of 258278-25-0, the publication is European Journal of Inorganic Chemistry (2022), 2022(16), e202200103, database is CAplus.

The mechanochem. syntheses of allyl and indenyl palladate complexes are reported. All compounds were obtained in quant. yields and microanalytically pure without the need of any workup. These complexes are stable in chlorinated and polar (DMSO or DMSO/H₂O solutions) solvents. In chlorinated solvents, they appear as ionic pairs of which crystals suitable for single x-ray diffraction studies have been obtained. Bonding and solvation properties are rationalized through scalar relativistic DFT calculations Moreover, most complexes showed excellent cytotoxicity towards ovarian cancer cell lines, with IC₅₀ values comparable or lower than cisplatin. The potent anticancer activity of two IPr^Cl and IPr*-based palladate complexes was examined in a high-grade serous ovarian cancer (HGSOC) patient-derived tumoroid. Moreover, the inhibition of the antioxidant enzyme thioredoxin reductase (TrxR) was noticed, and structure-activity relationships could be derived, suggesting the ROS detoxifying system is involved in the mode of action.

European Journal of Inorganic Chemistry published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, Synthetic Route of 258278-25-0.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Monsigny, Louis published the artcileActivated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde, Application of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Advanced Synthesis & Catalysis (2021), 363(19), 4590-4604, database is CAplus.

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 com. 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-analog 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 chem. 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 2^nd generation Hoveyda-Grubbs catalysts.

Advanced Synthesis & Catalysis published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, Application of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Spiridonov, Kirill A. published the artcilePhosphite-containing iridium polarization transfer catalysts for NMR signal amplification by reversible exchange, Formula: C27H39ClN2, the publication is Mendeleev Communications (2021), 31(4), 475-477, database is CAplus.

Two new iridium complexes with an N-heterocyclic carbine and phosphite ligands have been synthesized and characterized. Bubbling of parahydrogen through their solutions resulted in the formation of several hydride complexes. In the presence of pyridine, this process is accompanied by transfer of spin order from the mol. hydrogen to pyridine mols. undergoing dynamic exchange between free and complex-bound states.

Mendeleev Communications published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C13H9FO, Formula: C27H39ClN2.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Nambo, Masakazu published the artcileDevelopment of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is ACS Catalysis (2017), 7(2), 1108-1112, database is CAplus.

The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki-Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring of the sulfone facilitates the Pd-catalyzed activation of the C-SO₂ bonds. Cross-coupling reactions with fluorinated sulfone electrophiles are reported, leading to a variety of multiply arylated products in good yields. The reactivity of this unusual electrophile is benchmarked vs. common electrophiles and its use in iterative cross-couplings for concise synthesis of biol. active mols. is described.

ACS Catalysis published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Wessels, Alina published the artcileFormation of Breslow Intermediates from N-Heterocyclic Carbenes and Aldehydes Involves Autocatalysis by the Breslow Intermediate, and a Hemiacetal, HPLC of Formula: 258278-25-0, the publication is Angewandte Chemie, International Edition (2022), 61(23), e202117682, database is CAplus and MEDLINE.

Under aprotic conditions, the stoichiometric reaction of N-heterocyclic carbenes (NHCs) such as imidazolidin-2-ylidenes with aldehydes affords Breslow Intermediates (BIs), involving a formal 1,2-C-to-O proton shift. We herein report kinetic studies (NMR), complemented by DFT calculations, on the mechanism of this kinetically disfavored H-translocation. Variable time normalization anal. (VTNA) revealed that the kinetic orders of the reactants vary for different NHC-to-aldehyde ratios, indicating different and ratio-dependent mechanistic regimes. We propose that for high NHC-to-aldehyde ratios, the H-shift takes place in the primary, zwitterionic NHC-aldehyde adduct. With excess aldehyde, the zwitterion is in equilibrium with a hemiacetal, in which the H-shift occurs. In both regimes, the critical H-shift is auto-catalyzed by the BI. Kinetic isotope effects observed for R-CDO are in line with our proposal. Furthermore, we detected an H-bonded complex of the BI with excess NHC (NMR).

Angewandte Chemie, International Edition published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C8H11NO, HPLC of Formula: 258278-25-0.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Zhukhovitskiy, Aleksandr V. published the artcileMigratory Insertion of Carbenes into Au(III)-C Bonds, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Journal of the American Chemical Society (2018), 140(1), 466-474, database is CAplus and MEDLINE.

Migratory insertion of carbon-based species into transition-metal-carbon bonds is a mechanistic manifold of vast significance: it underlies the Fischer-Tropsch process, Mizoroki-Heck reaction, Ziegler-Natta and analogous late-transition-metal-catalyzed olefin polymerizations, and a number of carbonylative methods for the synthesis of ketones and esters, among others. Although this type of reactivity is well-precedented for most transition metals, gold constitutes a notable exception, with virtually no well-characterized examples known to date. Yet, the complementary reactivity of gold to numerous other transition metals would offer new synthetic opportunities for migratory insertion of carbon-based species into gold-carbon bonds. Here we report the discovery of well-defined Au(III) complexes that participate in rapid migratory insertion of carbenes derived from silyl- or carbonyl-stabilized diazoalkanes into Au-C bonds at temperatures ≥ -40 °C. Through a combined theor. and exptl. approach, key kinetic, thermodn., and structural details of this reaction manifold were elucidated. This study paves the way for homogeneous gold-catalyzed processes incorporating carbene migratory insertion steps.

Journal of the American Chemical Society published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C17H14N2O2, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Liu, Jiangjun published the artcileNickel-Catalyzed Intramolecular Desulfitative C-N Coupling: A Synthesis of Aromatic Amines, Synthetic Route of 258278-25-0, the publication is Journal of Organic Chemistry (2020), 85(8), 5702-5711, database is CAplus and MEDLINE.

A nickel-catalyzed intramol. C-N coupling reaction via SO₂ extrusion was presented. The use of a catalytic amount of BPh₃ allowed the transformation to take place under much milder conditions (60°C) than previously reported C-N coupling reactions by CO or CO₂ extrusion (160-180°C). In addition, this method displayed good functional group tolerance and versatility, as it can be applied to the synthesis of dialkyl aryl amines, alkyl diaryl amines and triaryl amines. The robustness of the desulfitative C-N coupling was demonstrated by three high-yielding gram-scale reactions.

Journal of Organic Chemistry published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, Synthetic Route of 258278-25-0.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Zhang, Gaopeng published the artcilePalladium-catalyzed allylic alkylation reaction of α-substituted benzyl nitriles with branched allyl carbonates, Application In Synthesis of 258278-25-0, the publication is Youji Huaxue (2020), 40(10), 3399-3409, database is CAplus.

Pd-catalyzed allylic alkylation reaction of α-substituted benzyl nitriles with branched allyl carbonates in the presence of bulkier N-heterocyclic carbene ligand was reported, which provided the corresponding allylated products in good yield with high regio- and diastereo-selectivity.

Youji Huaxue published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C15H24O2, Application In Synthesis of 258278-25-0.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Meng, Guangrong published the artcileA simple ¹H NMR method for determining the σ-donor properties of N-heterocyclic carbenes, HPLC of Formula: 258278-25-0, the publication is Tetrahedron Letters (2019), 60(4), 378-381, database is CAplus.

The σ-donor properties of NHC ligands (NHC = N-heterocyclic carbene) are crucial in controlling their interaction with transition metals, and as a consequence, to determine the selectivity and reactivity of NHCs in transition-metal-catalysis. Herein, we report a simple NMR method for estimating the σ-donor properties of NHC ligands based on a straightforward ¹H NMR measurement of ligand precursors. We present evaluation of σ-donating properties for a range of NHC ligands varied by structure and electronics that are relevant to transition-metal-catalysis. We expect that the simple measurement of σ-donating properties of NHCs, together with the known methods for evaluating sterics and π-backbonding, will enhance the understanding of the properties of NHCs in transition-metal-catalysis.

Tetrahedron Letters published new progress about 258278-25-0. 258278-25-0 belongs to imidazoles-derivatives, auxiliary class Achiral NHCs Ligands, name is 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, and the molecular formula is C27H39ClN2, HPLC of Formula: 258278-25-0.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem