Tag: 400-500

Product Details of 258278-25-0On June 7, 2022, Wessels, Alina; Klussmann, Martin; Breugst, Martin; Schlorer, Nils E.; Berkessel, Albrecht published an article in Angewandte Chemie, International Edition. The article was 《Formation of Breslow Intermediates from N-Heterocyclic Carbenes and Aldehydes Involves Autocatalysis by the Breslow Intermediate, and a Hemiacetal》. The article mentions the following:

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). 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: 258278-25-0Product Details 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.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

《New expanded-ring NHC platinum(0) complexes: Synthesis, structure and highly efficient diboration of terminal alkenes》 was written by Rzhevskiy, Sergey A.; Topchiy, Maxim A.; Lyssenko, Konstantin A.; Philippova, Anna N.; Belaya, Maria A.; Ageshina, Alexandra A.; Bermeshev, Maxim V.; Nechaev, Mikhail S.; Asachenko, Andrey F.. Recommanded Product: 258278-25-0 And the article was included in Journal of Organometallic Chemistry on April 15 ,2020. The article conveys some information:

The synthesis and structural characterization of novel Pt(0) complexes are reported. A number of (NHC)Pt(dvtms) (dvtms = 1,3-divinyl-1,1,3,3-tetramethyldisiloxane) complexes were studied in catalytic addition of B2Pin2 to terminal alkenes. The novel expanded ring N-heterocyclic carbene complex (7-Dipp)Pt(dvtms) showed highest performance, turnover numbers up to 3800 were achieved. The scope of the reaction was illustrated by 20 examples with a variety of alkyl, alkoxy, halogen, ester, ketone and acetal substituents. 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: 258278-25-0Recommanded Product: 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.Recommanded Product: 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

Agata, Ryosuke; Takaya, Hikaru; Matsuda, Hiroshi; Nakatani, Naoki; Takeuchi, Katsuhiko; Iwamoto, Takahiro; Hatakeyama, Takuji; Nakamura, Masaharu published an article on February 28 ,2019. The article was titled 《Iron-catalyzed cross coupling of aryl chlorides with alkyl grignard reagents: synthetic scope and Fe(II)/Fe(IV) mechanism supported by X-ray absorption spectroscopy and density functional theory calculations》, and you may find the article in Bulletin of the Chemical Society of Japan.Product Details of 258278-25-0 The information in the text is summarized as follows:

A combination of Fe(III) fluoride and 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene (SIPr) catalyzes the high-yielding cross coupling of an electron-rich aryl chloride with an alkyl Grignard reagent, which cannot be attained using other Fe catalysts. A variety of alkoxy- or amino-substituted aryl chlorides can be cross-coupled with various alkyl Grignard reagents regardless of the presence or absence of β-hydrogens in the alkyl group. A radical probe experiment using 1-(but-3-enyl)-2-chlorobenzene does not afford the corresponding cyclization product, therefore excluding the intermediacy of radical species. Solution-phase x-ray absorption spectroscopy (XAS) anal., with the help of d. functional theory (DFT) calculations, indicates the formation of a high-spin (S = 2) heteroleptic difluorido organoferrate(II), [MgX][Fe(II)F2(SIPr)(Me/alkyl)], in the reaction mixture DFT calculations also support a feasible reaction pathway, including the formation of a difluorido organoferrate(II) intermediate which undergoes a novel Lewis acid-assisted oxidative addition to form a neutral organoiron(IV) intermediate, which leads to an Fe(II)/Fe(IV) catalytic cycle, where the fluorido ligand and the Mg ion play key roles. 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: 258278-25-0Product Details of 258278-25-0)

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.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

Related Products of 258278-25-0On June 8, 2022, Scattolin, Thomas; Pessotto, Ilenia; Cavarzerani, Enrico; Canzonieri, Vincenzo; Orian, Laura; Demitri, Nicola; Schmidt, Claudia; Casini, Angela; Bortolamiol, Enrica; Visentin, Fabiano; Rizzolio, Flavio; Nolan, Steven P. published an article in European Journal of Inorganic Chemistry. The article was 《Indenyl and Allyl Palladate Complexes Bearing N-Heterocyclic Carbene Ligands: an Easily Accessible Class of New Anticancer Drug Candidates》. The article mentions the following:

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 IPrCl 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. 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: 258278-25-0Related Products 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.Related Products 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

《[(NHC)NiIIH]-Catalyzed Cross-Hydroalkenylation of Cyclopropenes with Alkynes: Cyclopentadiene Synthesis by [(NHC)NiII]-Assisted C-C Rearrangement》 was published in Angewandte Chemie, International Edition in 2019. These research results belong to Huang, Jian-Qiang; Ho, Chun-Yu. Recommanded Product: 258278-25-0 The article mentions the following:

The cross-hydroalkenylation/rearrangement cascade (HARC), using a cyclopropene, e.g., 3′,4′-dihydrospiro[2-cyclopropene-1,1′(2’H)-naphthalene] and alkyne RCCR1 (R = H, CH3, C2H5, (CH2)2CH3, OC2H5; R1 = CH2OCH3, CH2OC6H5, cyclohexyl, etc.) as substrate pairs was achieved for the first time by using new [(NHC)Ni(allyl)]BArF (Ar = mesityl, diisopropylphenyl, 3-pentyl) catalysts (NHCN-heterocyclic carbenes). By controlling the (NHC)NiIIH relative insertion reactivity with cyclopropene and alkyne, a broad scope of cyclopentadienes, e.g., I was obtained with high selectivity. The structural features of new (NHC)NiII catalyst were important for the success of the reaction. The mild reaction conditions employed may serve as an entry for exploring (NHC)NiII-assisted vinylcyclopropane rearrangement reactivity. The experimental part of the paper was very detailed, including the reaction process of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Recommanded Product: 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.Recommanded Product: 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

《Continuous Flow Synthesis of Sulfur- and Selenium-NHC Compounds (NHC=N-Heterocyclic Carbene)》 was written by Cauwenbergh, Thibault; Scattolin, Thomas; Simoens, Andreas; Tzouras, Nikolaos V.; Stevens, Christian V.; Nolan, Steven P.. Product Details of 258278-25-0 And the article was included in European Journal of Organic Chemistry on April 21 ,2022. The article conveys some information:

The first continuous flow syntheses of sulfur- and selenium-NHC (NHC=N-heterocyclic carbene) adducts in unprecedented short reaction times and high yields are reported. The importance of these species in coordination chem. or as efficient tools for determining the π-acceptor character of NHC ligands make any improvement in their synthesis a worthy goal. Thiourea derivatives bearing both saturated and unsaturated NHCs were obtained using NEt3 as a weak base (homogeneous setup) in conjunction with a bed of elemental sulfur (S8). The synthetic route proving optimal for selenoureas involves the use of a simple Se/K2CO3 heterogeneous microreactor design. The experimental process involved the reaction of 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

《Polyethylene Aerogels with Combined Physical and Chemical Crosslinking: Improved Mechanical Resilience and Shape-Memory Properties》 was published in Angewandte Chemie, International Edition in 2019. These research results belong to Khedaioui, Douriya; Boisson, Christophe; D’Agosto, Franck; Montarnal, Damien. Quality Control of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The article mentions the following:

While the introduction of polymers into aerogels strongly enhances their toughness, truly elastic monolithic aerogels which restore their dimensions upon extensive compression are still challenging to synthesize. In this context hydrophobic semi-crystalline polymers with low glass transition temperatures, and combined stiffness and flexibility, have only recently attracted attention. Shown here is that polyethylene aerogels with a low d., and combined chem. crosslinking and high crystallinity, display high moduli and excellent mech. resilience. To maximize the crystallinity of these aerogels while maintaining a high crosslinking d., polyethylene networks with well-defined segments were synthesized by hydrosilylation crosslinking of telechelic, vinyl-functionalized oligomers obtained from catalyzed chain-growth polymerization Recoverable deformations both above and below the melting temperature of polyethylene affords remarkable shape-memory properties. In the experiment, the researchers used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Quality Control 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) 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.Quality Control 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

HPLC of Formula: 258278-25-0On May 8, 2019 ,《Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines》 appeared in Journal of the American Chemical Society. The author of the article were Nishizawa, Akihiro; Takahira, Tsuyoshi; Yasui, Kosuke; Fujimoto, Hayato; Iwai, Tomohiro; Sawamura, Masaya; Chatani, Naoto; Tobisu, Mamoru. The article conveys some information:

Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants. 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: 258278-25-0HPLC 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

In 2020,Chemical Communications (Cambridge, United Kingdom) included an article by Wei, Yi-Ming; Ma, Xiao-Di; Wang, Lei; Duan, Xin-Fang. Application of 258278-25-0. The article was titled 《Iron-catalyzed stereospecific arylation of enol tosylates using Grignard reagents》. The information in the text is summarized as follows:

The stereospecific Fe-catalyzed arylation of enol tosylates with Grignard reagents was reported for the synthesis of Z- and E- tri/tetrasubstituted acrylates (Ar)(R)C=C(CO2R1)(R2) [R = Me, i-Pr, Ph, etc.; R1 = Me, Et; R2 = H, Me, Ph; Ar = Ph, 2-CNC6H4, 2-thienyl, etc.]. Various tri- or tetrasubstituted Z or E-enol tosylates of β-keto esters were arylated using common and Knochel-type Grignard reagents with complete stereofidelity. The precursors for Z/E-zimelidine, tamoxifen and other bioactive compounds were facilely prepared without precious and toxic transition metals. 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: 258278-25-0Application of 258278-25-0)

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 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

In 2022,Chemical Communications (Cambridge, United Kingdom) included an article by Huang, Shuai; Zhang, Gao-Peng; Jiang, Yang-Jie; Yu, Fei-Le; Ding, Chang-Hua; Hou, Xue-Long. Recommanded Product: 258278-25-0. The article was titled 《Pd-Catalyzed umpolung asymmetric allylic alkylation of hydrazones to vicinal tertiary and quaternary chiral carbon centers》. The information in the text is summarized as follows:

Diastereo- and enantioselective construction of vicinal tertiary and quaternary carbon centers is a great challenge in synthetic chem. Herein, a facile and efficient protocol to construct unsaturated azo compounds I [R1 = Ph, 4-FC6H4, 2-naphthyl, 2-thienyl, etc., R2 = Me; R1 = Ph, R2 = Et; R1R2 = (CH2)5; R3 = Ph, 4-MeOC6H4, 1,3-benzodioxol-5-yl, 2-furyl, etc.] with vicinal tertiary and quaternary chiral carbon centers in high yields with high regio-, diastereo- and enantioselectivities via Pd-catalyzed umpolung asym. allylic alkylation of hydrazones II with monosubstituted allylic pivalates R3CH:CHCH2OC(O)Bu-t by using Kundig-type chiral N-heterocyclic carbene as the ligand is reported. The control experiments revealed that the reaction proceeds via the inner-sphere mechanism. 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: 258278-25-0Recommanded Product: 258278-25-0)

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.Recommanded Product: 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