Category: 258278-25-0

Li, Jiang-Fei published the artcileConstruction 7-membered ring via Ni-Al bimetal-enabled C-H cyclization for synthesis of tricyclic imidazoles, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Nature Communications (2021), 12(1), 3070, database is CAplus and MEDLINE.

A direct construction of 7-membered rings via Ni-Al co-catalyzed unreactive C7-H cyclization of benzoimidazoles with alkenes, providing a series of tricyclic imidazoles such as I [R = Me, 2-FC₆H₄, BnO(CH₂)₂, etc.; R¹ = CF₃, 3-pyridyl, Bn, etc.; R² = H, 4-t-Bu, 4,5-F₂, etc.] in 40-98% yield and with up to 95:5 er was reported.

Nature 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 C27H39ClN2, 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

Sun, Qiao published the artcileCobalt-catalyzed C(sp²)-H/C(sp³)-H coupling via directed C-H activation and 1,5-hydrogen atom transfer, Synthetic Route of 258278-25-0, the publication is Organic Chemistry Frontiers (2018), 5(4), 582-585, database is CAplus.

The regioselective synthesis of 1-[2-[(benzylamino)methyl]phenyl]ethanones such as I [R = H, 3-Cl, 4-Ph, etc.; R¹ = Me, n-Pr; R² = Et, n-Bu; R¹R² = (CH₂)₃, (CH₂)₄, (CH₂)₅, etc.] via cobalt-catalyzed C(sp²)-H/C(sp³)-H cross-coupling reaction between various (E)-aryl imines and 2-bromobenzyl-protected secondary amines was reported. Promoted by a combination of a cobalt-N-heterocyclic carbene catalyst and Grignard reagent, the reaction was allowed for the introduction of α-aminoalkyl groups into the ortho position of the imine at a mild temperature The cobalt catalyst was proposed to play key roles in two distinct modes of C-H cleavage, i.e., directed C-H metalation and 1,5-hydrogen atom transfer.

Organic 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 C7H5Cl2NO, Synthetic Route of 258278-25-0.

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

Chen, Xuemeng published the artcileTransition-Metal-Catalyzed Transformation of Sulfonates via S-O Bond Cleavage: Synthesis of Alkyl Aryl Ether and Diaryl Ether, Recommanded Product: 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Organic Letters (2019), 21(22), 8879-8883, database is CAplus and MEDLINE.

The catalytic conversion of sulfonates, a versatile class of pharmaceutical intermediates, is usually based on C-O bond cleavage. In this paper, however, a rare transformation of sulfonates R¹SO₂OR² [R¹ = 2-pyridyl, 3-methyl-2-pyridyl, 5-trifluoromethyl-2-pyridyl, etc.; R² = Ph, 2-naphthyl, 3-quinolyl, Ph(CH₂)₃, 1-heptyl, 2-adamantyl, etc.] via S-O bond cleavage catalyzed by transition metal. Alkyl sulfonates underwent an intramol. desulfitative C-O coupling to form aryl alkyl ethers in the presence of a nickel catalyst, whereas aryl sulfonates performed similarly under palladium complex catalysis to give diaryl ethers. This transformation could tolerate a wide range of functionalities. Controlled experiments revealed that the 2-pyridyl group is necessary to promote the reaction as designed. Crossover experiments proved that this transformation might proceed partly in an intermol. pathway.

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

Liu, Xiaojie published the artcileNi-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation, SDS of cas: 258278-25-0, the publication is ACS Catalysis (2022), 12(15), 8904-8910, database is CAplus.

Herein, we report an efficient method for the Ni-catalyzed deoxygenative borylation of unprotected phenols and also demonstrate that this Ni-catalyzed phenolic C(sp²)-O transformation is applicable to the Suzuki-Miyaura-type and Heck-type cross-couplings of phenols. Investigations on the reaction intermediate have revealed that the achievement of general, mild deoxygenative cross-coupling reactions of phenols is ascribed to the conversion of phenols into the unusual O-phenyl-uroniums that feature active phenolic C(sp²)-O bonds. The Ni-complex intermediate resulting from an oxidative addition of a phenolic C(sp²)-O bond to monophosphine-supported Ni(0) catalyst was characterized and confirmed to be (PCy₃)₂Ni(Ar)(F) complex, offering exptl. evidence for the generally proposed C(sp²)-O oxidative addition step.

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, SDS of cas: 258278-25-0.

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

Zinser, Caroline M. published the artcileTowards environmentally friendlier Suzuki-Miyaura reactions with precursors of Pd-NHC (NHC = N-heterocyclic carbene) complexes, HPLC of Formula: 258278-25-0, the publication is Green Chemistry (2018), 20(14), 3246-3252, database is CAplus.

The preparation of [NHC·H][Pd(η³-R-allyl)Cl₂] complexes is disclosed and represents a facile, atom-economical, environmentally friendly and rapid synthesis. These palladates are immediate synthetic precursors to the well-known [Pd(NHC)(η³-R-allyl)Cl] complexes. Their activation leading to catalytically relevant species has been studied in the Suzuki-Miyaura reaction. The need for an activation step prior to the catalysis was examined The reaction scope showcases its ease and breadth in terms of functional group tolerance. Electron-donating and electron-withdrawing aryl chlorides and bromides were coupled effectively as well as heteroatom-containing and sterically hindered aryl halides. The catalytic reaction was conducted in ethanol with a weak and inexpensive inorganic base.

Green 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 C11H15N3O5, HPLC of Formula: 258278-25-0.

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

Deng, Yuchao published the artcileIron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow, HPLC of Formula: 258278-25-0, the publication is Chemistry – A European Journal (2019), 25(64), 14532-14535, database is CAplus and MEDLINE.

A selective, practical and fast iron-based cross-coupling reaction that enabled the formation of Csp-Csp³ and Csp²-Csp³ bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allowed the use of a supporting ligand to be avoided without eroding the reaction selectivity.

Chemistry – A European Journal 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

Wang, Lei published the artcileUnified Protocol for Fe-Based Catalyzed Biaryl Cross-Couplings between Various Aryl Electrophiles and Aryl Grignard Reagents, Related Products of imidazoles-derivatives, the publication is Journal of Organic Chemistry (2019), 84(9), 5176-5186, database is CAplus and MEDLINE.

The combination of commonly used FeCl₃/SIPr with Ti(OEt)₄/PhOM enabled a highly general iron-based catalyst system, which could efficiently catalyze the biaryl coupling reaction between various electrophiles (I, Br, Cl, OTs, OCONMe₂, OSO₂NMe₂) and common or functionalized aryl Grignard reagents with high functional group tolerance. Selective couplings of aryl iodides and bromides over the corresponding oxygen-based electrophiles have been achieved, and thus a terphenyl acid intermediate for anidulafungin was conveniently synthesized via an orthogonal coupling strategy.

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 C4H6F3NOS, Related Products of imidazoles-derivatives.

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

Liu, Yaxu published the artcileVersatile and Highly Efficient trans-[Pd(NHC)Cl₂(DMS/THT)] Precatalysts for C-N and C-C Coupling Reactions in Green Solvents, Synthetic Route of 258278-25-0, the publication is European Journal of Organic Chemistry (2022), 2022(14), e202200309, database is CAplus.

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.

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, Synthetic Route of 258278-25-0.

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

Hu, Rong-Bin published the artcileDirect Allylic C-H Bond Activation To Synthesize [Pd(η³-cin)(IPr)Cl] Complex: Application in the Allylation of Oxindoles, Application In Synthesis of 258278-25-0, the publication is ACS Catalysis (2017), 7(11), 7400-7404, database is CAplus.

N-heterocyclic carbenes (NHCs) was uncovered as an efficient ligand in promoting allylic C-H bond functionlizations. Notably, the catalytic [Pd(η³-cin)(IPr)Cl] complex (where cin = cinnamyl) was formed in situ from direct C-H activation of allylic precursors, and was obtained by way of one-pot strategy with available IPr·HCl and allylbenzene. The catalyst exhibits high regioselectivity and stereoselectivity of the allylic C-H alkylation with oxindoles with a broad scope.

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, Application In Synthesis of 258278-25-0.

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

Rzhevskiy, Sergey A. published the artcileNew expanded-ring NHC platinum(0) complexes: Synthesis, structure and highly efficient diboration of terminal alkenes, Safety of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride, the publication is Journal of Organometallic Chemistry (2020), 121140, database is CAplus.

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.

Journal of Organometallic 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, 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