Tag: 400-500

Nanda, Tanmayee; Biswal, Pragati; Pati, Bedadyuti Vedvyas; Banjare, Shyam Kumar; Ravikumar, Ponneri Chandrababu published an article on February 5 ,2021. The article was titled 《Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides》, and you may find the article in Journal of Organic Chemistry.Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The information in the text is summarized as follows:

Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) was explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation worked under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. Vinylic hydrogen in the product was proved that it is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive mols. such as procaine, estrone, and hymecromone demonstrated the robustness of this protocol. In the part of experimental materials, we found many familiar compounds, such as 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Low-Valent Group 14 Phosphinidenide Complexes [({SIDipp}P)2M] Exhibit P-M pπ-pπ Interaction (M=Ge, Sn, Pb)》 was published in Chemistry – A European Journal in 2020. These research results belong to Balmer, Markus; Franzke, Yannick J.; Weigend, Florian; von Haenisch, Carsten. Computed Properties of C27H39ClN2 The article mentions the following:

Herein, the synthesis of new low-valent Group 14 phosphinidenide complexes [({SIDipp}P)2M] exhibiting P-M pπ-pπ interactions (SIDipp = 1,3-bis(2,6-diisopropylphenyl)-imidazolidin-2-ylidene, M = Ge, Sn, Pb), is presented. These compounds were studied by structural, spectroscopic, and quantum-chem. methods. Furthermore, the monosubstituted compounds [(SIDippP)MX]2 (M = Sn, X=Cl; M = Pb, X = Br) are presented, which show dimeric structures instead of multiple bonding interaction. The results came from multiple reactions, including the reaction of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Computed Properties of C27H39ClN2)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Computed Properties of C27H39ClN2In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 258278-25-0On March 15, 2019, Yang, Jin published an article in Journal of Organometallic Chemistry. The article was 《Preparation and catalytic properties of the triphenylarsine and triphenylstibine-stabilized tri-heteroleptic NHC-Pd-allyl complexes》. The article mentions the following:

A series of triphenylarsine and triphenylstibine-stabilized tri-heteroleptic NHC-Pd-allyl complexes were synthesized and characterized. The solid-state structures of the complexes shown mononuclear carbene palladium complexes, in which, each palladium center was coordinated by an N-heterocyclic carbene, the η3-coordinated allyl moiety and an As or Sb donor. Further investigation of the Pd complexes as catalysts in Sonogashira coupling reaction was carried out and the obtained complexes exhibited good reactivities for aryl bromides. In addition to this study using 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, there are many other studies that have used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Application of 258278-25-0) was used in this study.

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Application of 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《N-Heterocyclic Olefin-Ligated Palladium(II) Complexes as Pre-Catalysts for Buchwald-Hartwig Aminations》 were Watson, Ian C.; Schumann, Andre; Yu, Haoyang; Davy, Emma C.; McDonald, Robert; Ferguson, Michael J.; Hering-Junghans, Christian; Rivard, Eric. And the article was published in Chemistry – A European Journal in 2019. Reference of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The author mentioned the following in the article:

New N-heterocyclic olefins (NHOs) are described with functionalization on the ligand heterocyclic backbone and terminal alkylidene positions. Various PdII-NHO complexes I (Ar = 2,6-iPr2C6H3; L = 3-chloropyridine; R = Me, RR =9,10-acenaphthylenediyl) and were prepared by cleavage of chloro-bridged dimers (I-L)2 with pyridine ligand; the complexes were evaluated as pre-catalysts in Buchwald-Hartwig aminations. Vinylogous complex [(Me2Dipp2Im-2-CH:CHCH2Pd)Cl2L] (13) was prepared by palladation of 1,3-Dipp2-4,5-dimethyl-2-(2-propenylidene)imidazoline. The most active system for catalytic C-N bond formation between hindered arylamine and haloarene substrates was accessed by combining a backbone methylated NHO with [Pd(cinnamyl)Cl]2 in the presence of NaOtBu as a base. In these active systems evidence suggests that catalysis is mediated by colloidal palladium metal, highlighting a different coordination ability of NHOs in comparison with commonly used N-heterocyclic carbene co-ligands.1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Reference of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride) was used in this study.

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Reference of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of C27H39ClN2On October 5, 2021 ,《Activated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde》 was published in Advanced Synthesis & Catalysis. The article was written by Monsigny, Louis; Piatkowski, Jakub; Trzybinski, Damian; Wozniak, Krzysztof; Nienaltowski, Tomasz; Kajetanowicz, Anna; Grela, Karol. The article contains the following contents:

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 2nd generation Hoveyda-Grubbs catalysts. The results came from multiple reactions, including the reaction of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Electric Literature of C27H39ClN2)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Electric Literature of C27H39ClN2In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In 2019,Organic & Biomolecular Chemistry included an article by Jang, Won Jun; Kang, Byung-Nam; Lee, Ji Hun; Choi, Yoon Mi; Kim, Chong-Hyeak; Yun, Jaesook. Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride. The article was titled 《NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes》. The information in the text is summarized as follows:

An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates. In addition to this study using 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, there are many other studies that have used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride) was used in this study.

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Spiridonov, Kirill A.; Kozinenko, Vitaly P.; Nikovsky, Igor A.; Pavlov, Alexander A.; Vol′khina, Tatyana N.; Nelyubina, Yulia V.; Kiryutin, Alexey S.; Yurkovskaya, Alexandra V.; Polezhaev, Alexander A.; Novikov, Valentin V.; Ivanov, Konstantin L. published an article in Mendeleev Communications. The title of the article was 《Phosphite-containing iridium polarization transfer catalysts for NMR signal amplification by reversible exchange》.Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The author mentioned the following in the article:

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. In the experiment, the researchers used many compounds, for example, 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.Application In Synthesis of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Versatile and Highly Efficient trans-[Pd(NHC)Cl2(DMS/THT)] Precatalysts for C-N and C-C Coupling Reactions in Green Solvents》 was written by Liu, Yaxu; Voloshkin, Vladislav A.; Scattolin, Thomas; Peng, Min; Van Hecke, Kristof; Nolan, Steven P.; Cazin, Catherine S. J.. Product Details of 258278-25-0 And the article was included in European Journal of Organic Chemistry on April 12 ,2022. The article conveys some information:

A straightforward synthetic procedure to well-defined, air- and moisture- stable trans-[Pd(NHC)Cl2(DMS/THT)] (NHC=IPr, SIPr, IMes, IPrCl, IPr*, IPr#) pre-catalysts was reported. These complexes were obtained by reacting NHC.HCl imidazolium salts with trans-[PdCl2(DMS/THT)2] precursors with the assistance of the weak base K2CO3 in green acetone at40°C. The scalability of this protocol was demonstrated. The catalytic activity of the synthesized complexes was studied in the Buchwald-Hartwig and Suzuki-Miyaura reactions. Remarkably, most of the synthesized complexes exhibited higher catalytic activity with respect to their PEPPSI congeners in the Buchwald-Hartwig amination in 2-MeTHF. In particular, complex trans-[Pd(IPr#)Cl2(DMS)] enabled the coupling of various (hetero)aryl chlorides and primary/secondary amines with a 0.2 mol% catalyst loading. In addition, trans-[Pd(IPr)Cl2(DMS)] showed excellent performance in the room-temperature Suzuki-Miyaura reaction involving various (hetero)aryl chlorides and aryl boronic acids. In summary, the synthesized complexes, especially trans-[Pd(NHC)Cl2(DMS)], was considered as greener alternatives to classical PEPPSI type catalysts based on the lower toxicity of the throw-away DMS ligand compared to 3-chloropyridine. In the experimental materials used by the author, we found 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Product Details of 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Product Details of 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of C27H39ClN2On September 30, 2020 ,《Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene》 was published in Chinese Journal of Polymer Science. The article was written by Li, Yan-Qing; Zhou, Jian; Xiao, Ru; Cai, Zheng-Guo. The article contains the following contents:

A series of novel quinolinyl imidazolidin-2-imine nickel complexes with different substituents on the imidazolidin-2-imine ligand were synthesized and characterized. The complexes in the presence of methylaluminoxane (MAO) as a cocatalyst catalyzed the copolymerization of norbornene (N) and styrene (S) or para-chlorostyrene (CS) with high activity (up to 1070 kg·mol-1·h-1). The installation of sterically bulky substituents on the imidazolidine-2-imine ligand was effective for the increase of the mol. weight and the comonomer content, affording high mol. weight copolymers with tunable CS content (0.57 mol%-11.7 mol%), in which the existence of Cl group can provide reaction site for the further functionalization of copolymers as well as the synthesis of graft or crosslinked polymers. The linear relationship between the comonomer content and the glass transition temperature of the copolymers and the monomer reactivity ratios in the copolymerization indicated the formation of the expected functionalized cyclic olefin copolymers (COC). In the experiment, the researchers used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Synthetic Route of C27H39ClN2)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Synthetic Route of C27H39ClN2In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

HPLC of Formula: 258278-25-0On June 5, 2019, Han, Bo; Ma, Pengchen; Cong, Xuefeng; Chen, Hui; Zeng, Xiaoming published an article in Journal of the American Chemical Society. The article was 《Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study》. The article mentions the following:

Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodn. stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theor. mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs. In the experimental materials used by the author, we found 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0HPLC of Formula: 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.HPLC of Formula: 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem