Tag: 400-500

In 2019,European Journal of Organic Chemistry included an article by Zens, Anna; Bauer, Florian; Kolb, Benedikt; Mannchen, Fabian; Seubert, Philipp; Forschner, Robert; Flaig, Kim S.; Koehn, Andreas; Kunz, Doris; Laschat, Sabine. COA of Formula: C27H39ClN2. The article was titled 《Ni(NHC) Catalyzed Rearrangement of 1-Acyl-2-vinylcyclopropanes: Tackling a Mechanistic Puzzle by Combined Experimental and Computational Studies》. The information in the text is summarized as follows:

The Ni(NHC) catalyzed rearrangement of 1-acyl-2-vinylcyclopropanes to the corresponding 4-acyl-cyclopent-1-enes is highly promising for the synthesis of keto-functionalized annelated bi- and tricyclic subunits of natural products. Therefore, we investigated the catalytic activity of Ni(NHC) complexes in the rearrangement of 1-acyl-2-vinylcyclopropanes with different ring sizes and substitution patterns. Surprising effects regarding substrate scope and stereoselectivity of the Ni(NHC) catalyzed vinylcyclopropane-cyclopentene rearrangement were observed Only vinylcyclopropanes with 1-Me, 1-Ph, 1,2-dialkyl or 2-phenyl-substitution at the vinyl moiety could be rearranged successfully. Moreover, an endo-configuration on the cyclopropane ring was required for successful rearrangement. By treatment of the vinylcyclopropanes with Rh catalysts or Lewis acids, the involvement of Lewis acid catalysis could be ruled out. In order to understand these exptl. results and to rationalize the reactivity of the Ni(NHC) complexes computational studies were performed, which provided insights into mechanistic details. 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: 258278-25-0COA of Formula: C27H39ClN2)

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.COA of Formula: C27H39ClN2In 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 《Crystalline Divinyldiarsenes and Cleavage of the As:As Bond》 were Sharma, Mahendra K.; Blomeyer, Sebastian; Neumann, Beate; Stammler, Hans-Georg; Ghadwal, Rajendra S.. And the article was published in Chemistry – A European Journal in 2019. Computed Properties of C27H39ClN2 The author mentioned the following in the article:

The first divinyldiarsenes [{(NHC)C(Ph)}As]2 (NHC=IPr 3 a, SIPr 3 b; IPr=C{(NAr)CH}2; SIPr=C{(NAr)CH2}2; Ar=2,6-iPr2C6H3) are reported. Compounds 3 a and 3 b were prepared by the reduction of corresponding chlorides {(NHC)C(Ph)}AsCl2 (NHC=IPr 2 a, SIPr 2 b) with Mg. Calculations revealed a small HOMO-LUMO energy gap of 3.86 (3 a) and 4.24 eV (3 b). Treatment of 3 a with (Me2S)AuCl led to the cleavage of the As:As bond to restore 2 a, which is expected to proceed via the diarsane [{(IPr)C(Ph)}AsCl]2 (4). Remarkably, 4 as well as 2 a can be selectively accessed on treatment of 3 a with an appropriate amount of C2Cl6. Moreover, 3 a readily reacts with PhEEPh (E=Se or Te) at room temperature to give {(IPr)C(Ph)}As(EPh)2 (E=Se 5 a; Te 5 b), revealing the cleavage of As:As and E-E bonds and the formation of As-E bonds. Such highly selective stepwise oxidation (3a → 4 → 2a) and bond metathesis (3a → 5a,b) reactions are unprecedented in main-group chem. The experimental process involved 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) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.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

In 2019,Chemistry – A European Journal included an article by Rottschaefer, Dennis; Sharma, Mahendra K.; Neumann, Beate; Stammler, Hans-Georg; Andrada, Diego M.; Ghadwal, Rajendra S.. Quality Control of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride. The article was titled 《A Modular Access to Divinyldiphosphenes with a Strikingly Small HOMO-LUMO Energy Gap》. The information in the text is summarized as follows:

The olefinic C-H bond functionalization of (NHC)CHPh (NHC = IPr =C{(NAr)CH}2 1; SIPr = C{(NAr)CH2}2 2; Ar = 2,6-iPr2C6H3), derived from classical N-heterocyclic carbenes (NHCs), with PCl3 affords the dichlorovinylphosphines {(NHC)C(Ph)}PCl2 (NHC = IPr 3, SIPr 4). Two-electron reduction of 3 and 4 with magnesium leads to the formation of the divinyldiphosphenes [{(NHC)C(Ph)}P]2 (NHC = IPr 5, SIPr 6) as crystalline solids. Unlike literature-known diphosphenes, which are mostly yellow or orange, 5 is a green whereas 6 is a purple solid. Although the P:P bond lengths of 5 (2.062(1)) and 6 (2.055(1) Å) are comparable to those of the known diphosphenes (2.02-2.08 Å), the C-P bond lengths of 5 (1.785(1)) and 6 (1.797(1) Å) are, however, considerably shorter than a Csp2-P single bond length (1.85 Å), indicating a considerable π-conjugation between C:C and P:P moieties. The HOMO-LUMO energy gap for 5 (4.15) and 6 (4.52 eV) is strikingly small and thus the narrowest among the diphosphenes (>4.93 eV) reported as yet. Consequently, 5 readily undergoes P:P bond cleavage at room temperature on treatment with sulfur to form the unique dithiophosphorane {(IPr)C(Ph)}P(S)2 7. Interestingly, reaction of 5 with selenium gives the selenadiphosphirane [{(IPr)C(Ph)}P]2Se 8 with an intact P-P bond. 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: 258278-25-0Quality 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) has been employed in an efficient, one-pot synthesis of N-heterocyclic carbene-allylpalladium complexes.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

《Ni(COD)(DQ): An Air-Stable 18-Electron Nickel(0)-Olefin Precatalyst》 was written by Tran, Van T.; Li, Zi-Qi; Apolinar, Omar; Derosa, Joseph; Joannou, Matthew V.; Wisniewski, Steven R.; Eastgate, Martin D.; Engle, Keary M.. Related Products of 258278-25-0 And the article was included in Angewandte Chemie, International Edition on April 27 ,2020. The article conveys some information:

We report that Ni(COD)(DQ) (COD = 1,5-cyclooctadiene, DQ = duroquinone), an air-stable 18-electron complex originally described by Schrauzer in 1962, is a competent precatalyst for a variety of nickel-catalyzed synthetic methods from the literature. Due to its apparent stability, use of Ni(COD)(DQ) as a precatalyst allows reactions to be conveniently performed without use of an inert-atm. glovebox, as demonstrated across several case studies. The experimental process involved the reaction of 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

Xiao, Junzhe; Cui, Yifan; Li, Can; Xu, Haibo; Zhai, Yizhan; Zhang, Xue; Ma, Shengming published their research in Angewandte Chemie, International Edition on December 1 ,2021. The article was titled 《Room Temperature Allenation of Terminal Alkynes with Aldehydes》.Computed Properties of C27H39ClN2 The article contains the following contents:

A gold-catalyzed room temperature allenation of terminal alkynes (ATA) with aldehydes affording 1,3-disubstituted allenes with diverse functional groups was developed by identifying a gold(I) catalyst and an amine. The practicality of this reaction had been demonstrated by a ten gram-scale synthesis and the synthetic potentials have been demonstrated via various transformations and formal total synthesis of (-)-centrolobine. Mechanistic studies revealed that the gold catalyst, the aldehyde effect, the fluoroalkyl hydroxyl solvent (TFE or HFIP) and the structure of amine were vital in this room temperature ATA reaction. 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: 258278-25-0Computed Properties of C27H39ClN2)

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.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

HPLC of Formula: 258278-25-0On March 29, 2021, Mazars, Francois; Hrubaru, Madalina; Tumanov, Nikolay; Wouters, Johan; Delaude, Lionel published an article in European Journal of Organic Chemistry. The article was 《Synthesis of Azolium-2-dithiocarboxylate Zwitterions under Mild, Aerobic Conditions》. The article mentions the following:

Twelve imidazolium-, imidazolinium-, or benzimidazolium-2-dithiocarboxylate zwitterions with aliphatic or aromatic substituents on their nitrogen atoms, including four new unsym. 1-alkyl-3-arylimidazolium derivatives, were obtained in high yields (62-96%) upon reaction of azolium salts with CS2 and Cs2CO3 in acetonitrile at room temperature Compared to the previous strategies devised for the synthesis of NHC·CS2 betaines, this novel procedure relied on an innocuous, weak base and could be applied under mild aerobic conditions. All the new compounds were fully characterized by various anal. techniques and the mol. structures of two of them were determined by XRD anal. An associative mechanism involving the concerted reaction of the azolium salts with both CS2 and CO32- was tentatively proposed to account for the formation of the zwitterionic adducts without the intervention of free carbenes. This would explain the good results obtained with a weak inorganic base that lacks the strength needed to deprotonate the azolium salt substrates. 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: 258278-25-0HPLC 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

Sakurai, Shun; Inagaki, Tetsuya; Kodama, Takuya; Yamanaka, Masahiro; Tobisu, Mamoru published an article on January 26 ,2022. The article was titled 《Palladium-Catalyzed Siloxycyclopropanation of Alkenes Using Acylsilanes》, and you may find the article in Journal of the American Chemical Society.Reference of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The information in the text is summarized as follows:

Currently, catalytically transferable carbenes are limited to electron-deficient and neutral derivatives, and electron-rich carbenes bearing an alkoxy group (i.e., Fischer-type carbenes) cannot be used in catalytic cyclopropanation because of the lack of appropriate carbene precursors. We report herein that acylsilanes can serve as a source of electron-rich carbenes under palladium catalysis, enabling cyclopropanation of a range of alkenes. This reactivity profile is in sharp contrast to that of metal-free siloxycarbenes, which are unreactive toward normal alkenes. The resulting siloxycyclopropanes serve as valuable homoenolate equivalent, allowing rapid access to elaborate β-functionalized ketones. The experimental process involved the reaction of 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)

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

HPLC of Formula: 258278-25-0On March 29, 2021, Mazars, Francois; Hrubaru, Madalina; Tumanov, Nikolay; Wouters, Johan; Delaude, Lionel published an article in European Journal of Organic Chemistry. The article was 《Synthesis of Azolium-2-dithiocarboxylate Zwitterions under Mild, Aerobic Conditions》. The article mentions the following:

Twelve imidazolium-, imidazolinium-, or benzimidazolium-2-dithiocarboxylate zwitterions with aliphatic or aromatic substituents on their nitrogen atoms, including four new unsym. 1-alkyl-3-arylimidazolium derivatives, were obtained in high yields (62-96%) upon reaction of azolium salts with CS2 and Cs2CO3 in acetonitrile at room temperature Compared to the previous strategies devised for the synthesis of NHC·CS2 betaines, this novel procedure relied on an innocuous, weak base and could be applied under mild aerobic conditions. All the new compounds were fully characterized by various anal. techniques and the mol. structures of two of them were determined by XRD anal. An associative mechanism involving the concerted reaction of the azolium salts with both CS2 and CO32- was tentatively proposed to account for the formation of the zwitterionic adducts without the intervention of free carbenes. This would explain the good results obtained with a weak inorganic base that lacks the strength needed to deprotonate the azolium salt substrates. 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: 258278-25-0HPLC 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

Sakurai, Shun; Inagaki, Tetsuya; Kodama, Takuya; Yamanaka, Masahiro; Tobisu, Mamoru published an article on January 26 ,2022. The article was titled 《Palladium-Catalyzed Siloxycyclopropanation of Alkenes Using Acylsilanes》, and you may find the article in Journal of the American Chemical Society.Reference of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The information in the text is summarized as follows:

Currently, catalytically transferable carbenes are limited to electron-deficient and neutral derivatives, and electron-rich carbenes bearing an alkoxy group (i.e., Fischer-type carbenes) cannot be used in catalytic cyclopropanation because of the lack of appropriate carbene precursors. We report herein that acylsilanes can serve as a source of electron-rich carbenes under palladium catalysis, enabling cyclopropanation of a range of alkenes. This reactivity profile is in sharp contrast to that of metal-free siloxycarbenes, which are unreactive toward normal alkenes. The resulting siloxycyclopropanes serve as valuable homoenolate equivalent, allowing rapid access to elaborate β-functionalized ketones. The experimental process involved the reaction of 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)

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

《Direct Azidation of Phenols》 was published in European Journal of Organic Chemistry in 2019. These research results belong to Kitamura, Mitsuru; Murakami, Kento; Koga, Tatsuya; Eto, Takashi; Ishikawa, Akihiro; Shimooka, Hirokazu; Okauchi, Tatsuo. Formula: C27H39ClN2 The article mentions the following:

Direct azidation of phenols was developed. By treating chloroimidazolinium chloride I and sodium azide with phenol in the presence of a secondary amine in methoxyethanol, ortho-azidation of phenol was achieved. After reading the article, we found that the author used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Formula: 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.Formula: C27H39ClN2In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem