Category: 258278-25-0

Jang, Won Jun published the artcileNHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes, Formula: C27H39ClN2, the publication is Organic & Biomolecular Chemistry (2019), 17(21), 5249-5252, database is CAplus and MEDLINE.

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.

Organic & Biomolecular 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, Formula: C27H39ClN2.

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

Sakurai, Shun published the artcilePalladium-Catalyzed Siloxycyclopropanation of Alkenes Using Acylsilanes, Computed Properties of 258278-25-0, the publication is Journal of the American Chemical Society (2022), 144(3), 1099-1105, database is CAplus and MEDLINE.

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.

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 C27H39ClN2, Computed Properties of 258278-25-0.

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

Zhao, Chao-Yang published the artcilePd-Catalyzed Redox Divergent Coupling of Ketones with Terpenols, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is ACS Catalysis (2021), 11(12), 6825-6834, database is CAplus.

A Pd-catalyzed redox divergent coupling of ketones e.g., 6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one with terpenols like trans-geraniol, (E,E)-farnesyl alc. and (E)-phytol has been developed to access α-substituted ketones, e.g., 6-isopentyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one with varying degrees of unsaturation The control of oxidation states of the product is facilitated by employing different additives. With the aid of BnOH as an external hydrogen source, a reductive coupling pathway is thermodynamically favored. The use of LiBr as the additive will reduce the reactivity of Pd-H to divert the selectivity toward α,β-unsaturated ketones. By switching the solvent from toluene to chlorobenzene, the active species Pd-H will be fully quenched to enable oxidative coupling. Gram-scale reaction with lower catalyst loading (0.5 mol%) was also accomplished to highlight the practicability of this protocol. Furthermore, detailed exptl. studies were carried out to elucidate the reaction mechanism and the factors enabling manipulation of the redox selectivity. This redox divergent coupling protocol provides an important complement for known precedents on Tsuji-Trost allylation of ketones.

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 C10H11FN2O2S, 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

Kang, Byungjoon published the artcilePhotoredox mediated nickel catalyzed C(sp³)-H thiocarbonylation of ethers, HPLC of Formula: 258278-25-0, the publication is Chemical Science (2017), 8(9), 6613-6618, database is CAplus and MEDLINE.

The first direct C(sp³)-H thiocarbonylation reaction is achieved by visible light photoredox/Ni dual catalysis. The thioester group of thiobenzoate 4-F₃CC₆H₄C(O)SR (R = 4-FC₆H₄CH₂, 3-H₃COC₆H₄, 2-naphthyl, etc.) is transferred to the α-oxy carbon of various cyclic/acyclic ethers such as THF, tetrahydropyran, 1,4-dioxane, diethylether, anisole, and tert-butylmethylether, which is opposite to the commonly expected chem. reactivity involving acyl group transfer via the weaker C(acyl)-S activation. Through mechanistic studies, it was proposed that the reaction has been initiated by photocatalytic reduction and fragmentation of the thioester into an acyl radical and a thiolate. A nickel complex binds to the thiolate and induces the decarbonylation of the acyl radical to form an aryl radical, which abstracts hydrogen from the α-oxy carbon of the ether. The resulting α-oxy C(sp³) centered radical re-binds to the (RS)(CO)Ni complex, which undergoes CO migratory insertion and reductive elimination to give the desired thioester product RSC(O)R¹ (R¹ = tetrahydrofuran-2-yl, dioxan-2-yl, tetrahydropyran-2-yl, etc.).

Chemical Science 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

Mazars, Francois published the artcileSynthesis of Azolium-2-dithiocarboxylate Zwitterions under Mild, Aerobic Conditions, Quality Control of 258278-25-0, the publication is European Journal of Organic Chemistry (2021), 2021(13), 2025-2033, database is CAplus.

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 CO₃^2- 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.

European 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, Quality Control of 258278-25-0.

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

Saper, Noam I. published the artcileMechanistic Investigations of the Hydrogenolysis of Diaryl Ethers Catalyzed by Nickel Complexes of N-Heterocyclic Carbene Ligands, Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Journal of the American Chemical Society (2017), 139(48), 17667-17676, database is CAplus and MEDLINE.

Recent interest in the valorization of lignin has led to reactions involving the cleavage of strong aromatic C-O bonds. However, few exptl. mechanistic studies of these reactions have been published. We report detailed mechanistic anal. of the hydrogenolysis of diaryl ethers catalyzed by the combination of Ni(COD)₂ (COD = 1,5-cyclooctadiene) and an N-heterocyclic carbene (NHC). Experiments on the catalytic reaction indicated that NaOt-Bu was necessary for catalysis, but kinetic anal. showed that the base is not involved in the rate-limiting C-O bond cleavage. The resting state of the catalyst is an NHC-Ni(η⁶-arene) complex. Substitution of the coordinated solvent with diaryl ether allowed isolation of a diaryl ether-bound Ni complex. Rate-limiting C-O bond cleavage occurs to generate a three-coordinate product of oxidative addition, a metallacyclic version of which has been prepared independently. Stoichiometric studies show that arene and phenol products are released following reaction with H₂. NaOt-Bu was found to deprotonate the phenol product and to prevent formation of inactive Ni^I dimers.

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 C27H39ClN2, Name: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride.

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

Huang, Jian-Qiang published the artcile[(NHC)Ni^IIH]-Catalyzed Cross-Hydroalkenylation of Cyclopropenes with Alkynes: Cyclopentadiene Synthesis by [(NHC)Ni^II]-Assisted C-C Rearrangement, Quality Control of 258278-25-0, the publication is Angewandte Chemie, International Edition (2019), 58(17), 5702-5706, database is CAplus and MEDLINE.

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)Ni^IIH 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)Ni^II catalyst were important for the success of the reaction. The mild reaction conditions employed may serve as an entry for exploring (NHC)Ni^II-assisted vinylcyclopropane rearrangement reactivity.

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 C27H39ClN2, Quality Control of 258278-25-0.

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

Miralles, Nuria published the artcileCopper-Mediated S_N2′ Allyl-Alkyl and Allyl-Boryl Couplings of Vinyl Cyclic Carbonates, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Organic Letters (2017), 19(22), 6096-6099, database is CAplus and MEDLINE.

A method for the Cu-catalyzed borylmethylation and borylation of vinyl cyclic carbonates through an S_N2′ mechanism is reported. These singular reactions involve selective S_N2′ allylic substitutions with concomitant ring opening of the cyclic carbonate and with extrusion of CO₂ and formation of a useful hydroxyl functionality in a single step. The stereoselectivity of the homoallylic borylation and allylic borylation processes can be controlled, and synthetically useful unsaturated (E)-pent-2-ene-1,5-diols and (E)-but-2-ene-1,4-diols are accessed.

Organic 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, 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

Lee, Shao-Chi published the artcileNickel-catalyzed exo-selective hydroacylation/Suzuki cross-coupling reaction, Synthetic Route of 258278-25-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2019), 55(99), 14984-14987, database is CAplus and MEDLINE.

The first nickel-catalyzed intramol. hydroacylation/Suzuki cross coupling cascade of phenylboronic acid neopentyl glycol esters I (R = Ph, anthracen-9-yl, thiophen-2-yl, etc.) with a broad range of o-allylbenzaldehydes 2-CH₂=CHCH₂-4-R³-5-R²-6-R¹C₆HCHO (R¹ = H, R² = H, OMe; R¹R² = CH=CHCH=CH; R³ = H, OMe, Me, F) has been developed. This strategy shows high regioselectivity and step economy in the construction of two C-C bonds via aldehyde C-H bond activation, affording valuable indanones II with high efficiency.

Chemical Communications (Cambridge, United Kingdom) 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

Veenboer, Richard M. P. published the artcileExpedient Syntheses of Neutral and Cationic Au(I)-NHC Complexes, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Organometallics (2017), 36(18), 3645-3653, database is CAplus.

The synthesis and isolation of Au(I) precatalysts often requires the generation of several isolable intermediates as well as numerous purification steps. New protocols for the expedient synthesis of neutral [Au(OH)(NHC)] and [Au(CH₂COCH₃)(NHC)] species from [AuCl(NHC)] or [AuCl(DMS)] precursors bearing a variety of N-heterocyclic carbene (NHC) ligands are presented. These methods can be employed in a telescoping manner for the synthesis of catalytically relevant [Au(NTf₂)(NHC)] and [Au(NHC)(NCCH₃)][BF₄] complexes. These attractive methods are straightforward and practical leading to various complexes in high isolated yields and purity.

Organometallics 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 C13H26N2, 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