Month: December 2022

Penner, Page M. published the artcileGeneration and Reactions of ε-Carbonyl Cations via Group 13 Catalysis, SDS of cas: 151-10-0, the main research area is electrophilic aromatic substitution carbonyl cation allylation catalyst; allylation; catalysis; electrophilic aromatic substitution; umpolung; ε-carbonyl cations.

The generation of ε-carbonyl cations and their reactions with nucleophiles is accomplished readily without transition metal cation stabilization, using the ε-bromide dienoate or dienone starting materials and GaCl3 or InCl3 catalysis. Arene nucleophiles are somewhat more straightforward than allyltrimethylsilane, but allyltrimethylsilane and propiophenone trimethysilyl enol ether each react successfully with InCl3 catalysis. The viability of these cations is supported by DFT calculations

Molecules published new progress about Allylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, SDS of cas: 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yurino, Taiga published the artcileFriedel-Crafts-type Allylation of Phenol Derivatives Catalyzed by In Situ-Generated Silyl Cyanometallates, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is Friedel Crafts allylation phenol derivative catalyzed silyl cyanometalate intermediate; allylic phosphate Friedel Crafts allylation palladium silver catalyzed cyanotrimethylsilane; anisole para allylated regioselective preparation.

Authors successfully demonstrated that Friedel-Crafts-type allylation of phenol derivatives and allylic phosphates is catalyzed by the AgTFA/trimethylsilyl cyanide (Me3SiCN) and Pd(OAc)2/Me3SiCN combined systems to afford the C-allylated product in a highly regioselective manner. The corresponding silyl cyanometallates generated in situ are proposed to be the active catalytic species. Lewis acidity of the reversibly formed ion pairs is appropriately regulated for this reaction. The para-allylated anisole and phenol derivatives are selectively obtained. The para-substituted ones are converted to the ortho-allylated products. The reactivity of the catalytic systems is strongly dependent on the electronic nature of both electrophile and nucleophile. Substitution of an aromatic ring on the allylic phosphate is essential for the reaction. Thus, the competitive reaction of a 1 : 1 mixture of cinnamyl and simple allyl phosphates affords only the cinnamyl-substituted product.

Asian Journal of Organic Chemistry published new progress about Allylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Recommanded Product: 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Ma, Pengju published the artcilePhotocatalyst- and additive-free decarboxylative alkylation of N-aryl tetrahydroisoquinolines induced by visible light, Formula: C9H10O3, the main research area is alkyl aryl tetrahydroisoquinoline preparation; tetrachlorohydroxyphthalimide alkyl ester aryl tetrahydroisoquinoline decarboxylative alkylation.

Synthesis of C-1 alkylated tetrahydroisoquinoline products I (R = Pr, 4-oxocyclohexyl, oxan-4-yl, etc.; R1 = Ph, pyridin-4-yl, naphthalen-1-yl, etc.; R2 = H. MeO) and II via a visible light induced decarboxylative alkylation of N-aryl tetrahydroisoquinolines III (X = H) and 9-methyl-2-phenyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole has been developed using tetrachloro-N-hydroxyphthalimide esters IV as alkylation agents. This redox-neutral reaction can proceed without the assistance of photocatalysts, transition metals and external additives by irradiation with blue LEDs. Preliminary mechanistic studies indicated that this transformation probably proceeded through an electron donor-acceptor complex involved radical process.

Organic Chemistry Frontiers published new progress about Alkylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Svec, Riley L. published the artcileImidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations, Safety of 4-Methoxyphenylacetic acid, the main research area is repurpose imidazotetrazine weighable diazomethane synthon esterification cyclopropanation; alkylation; cyclopropanation; diazo compounds; diazomethane; imidazotetrazines.

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chem. of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that Me ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a com. available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

Angewandte Chemie, International Edition published new progress about Alkylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Safety of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Schiesser, Stefan published the artcileN-Trifluoromethyl Amines and Azoles: An Underexplored Functional Group in the Medicinal Chemist’s Toolbox, Formula: C8H11NO, the main research area is trifluoromethyl amine azole synthesis solubility permeability drug discovery.

Introducing trifluoromethyl groups is a common strategy to improve the properties of biol. active compounds However, N-trifluoromethyl moieties on amines and azoles are very rarely used. To evaluate their suitability in drug design, we synthesized a series of N-trifluoromethyl amines and azoles, determined their stability in aqueous media, and investigated their properties. We show that N-trifluoromethyl amines are prone to hydrolysis, whereas N-trifluoromethyl azoles have excellent aqueous stability. Compared to their N-Me analogs, N-trifluoromethyl azoles have a higher lipophilicity and can show increased metabolic stability and Caco-2 permeability. Furthermore, N-trifluoromethyl azoles can serve as bioisosteres of N-iso-Pr and N-tert-Bu azoles. Consequently, we suggest that N-trifluoromethyl azoles are valuable substructures to be considered in medicinal chem.

Journal of Medicinal Chemistry published new progress about Alkylation. 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Formula: C8H11NO.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Das, Kanu published the artcileN-Alkylation of Amines Catalyzed by a Ruthenium-Pincer Complex in the Presence of in situ Generated Sodium Alkoxide, Recommanded Product: 4-Methoxy-N-methylaniline, the main research area is secondary amine preparation density functional theory; alc primary amine alkylation ruthenium catalyst.

The use of ruthenium-NNN-pincer complexes of the type (R2NNN)RuCl2(PPh3) (R = tBu, iPr, Cy and Ph) for the catalytic N-alkylation of primary amines R-NH2 (R = Ph, propan-2-yl, thiophen-2-ylmethyl, etc.) under solvent-free conditions were reported. For the first time, the base that is required to promote these reactions is generated in situ from the alcs. R1-OH (R1 = Bu, (4-fluorophenyl)methyl, furan-2-ylmethyl, etc.) by the use of sodium. The resulting sodium alkoxide regenerates the alcs. substrate while acting as the water scavenger thus mitigating the need of an addnl. base. Among the catalysts screened, (tBu2NNN)RuCl2(PPh3) (0.02 mol-%) gives very high turnovers and good yields at 140 °C. The (tBu2NNN)RuCl2(PPh3) catalyzed N-alkylation tolerates a variety of amine and alc. substrates. While excellent turnover (29000) was obtained for the (tBu2NNN)RuCl2(PPh3) (0.002 mol-%) catalyzed alkylation of aniline with cyclohexyl methanol, the turnovers obtained in the corresponding catalytic methylation of p-anisidine was also very high (12000). The (tBu2NNN)RuCl2(PPh3) catalyzed reactions have also been accomplished under open-vessel conditions resulting in a net dehydrogenative coupling reaction. This protocol has been used to transform benzene-1,2-diamine to benzimidazoles I (R2 = H, F, OMe) with high productivity (12000 turnovers). DFT studies indicate that while β-hydride elimination is rate-determining (RDTS: 24.31 kcal/mol) for the alc. dehydrogenation segment which is endothermic, insertion of the imine is rate-determining (RDTS: 11.26 kcal/mol) for its hydrogenation that is exothermic.

European Journal of Organic Chemistry published new progress about Alkylation. 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Recommanded Product: 4-Methoxy-N-methylaniline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Kai published the artcileEnhanced Acidity and Activity of Aluminum/Gallium-Based Ionic Liquids Resulting from Dynamic Anionic Speciation, COA of Formula: C8H10O2, the main research area is acidity activity aluminum gallium based ionic liquid anionic speciation; Friedel Crafts acylation alkylation reaction catalyst.

To explore if the catalytic activity of single-metal species in halometallate catalysts can be enhanced with mixed-metal species, aluminum and gallium were simultaneously introduced to prepare a mixed-metal ionic liquid (IL) through a one-pot reaction of [HN222]Cl, AlCl3, and GaCl3 in various amounts The Lewis acidity in Friedel-Crafts acylation and alkylation reactions of these IL compositions were evaluated and all mixed-metal [HN222][xAlCl3 + (2 – x)GaCl3]Cl ILs exhibited higher catalytic activity than AlCl3, GaCl3, [HN222][Al2Cl7], or [HN222][Ga2Cl7]. The broadening in 27Al NMR of these ILs indicates the presence of dynamic anionic species, whereas matrix-assisted laser-desorption ionization time-of-flight (MALDI-TOF) and acetonitrile-probed Fourier transform IR (FT-IR) analyses correlates the structure-activity relationship, for instance, identifying the presence of mixed-metal-containing [Cl2GaOClAlClOGaCl2]- species in the better-performing ILs.

ACS Catalysis published new progress about Alkylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, COA of Formula: C8H10O2.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Navale, Balu S. published the artcilePropargyl α-aryl-α-diazoacetates as robust reagents for the effective C-H bond functionalization of 1,3-diketones via scandium catalysis, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is propargyl aryl dicarbonyl compound preparation; diketone propargyl aryl diazoacetate alkylation scandium catalyst.

Propargyl α-aryl-α-diazoacetates RC(=N2)C(O)OCH2CCH [R = 4-ClC6H4, naphthalen-2-yl, 3,4-(H3CO)2C6H3, etc.] a new class of reagents is developed for the effective C-H bond functionalization of 1,3-diketones R1C(O)CH2C(O)R1 (R1 = Me, Et, Ph, 4-H3CC6H4, 4-H3COC6H4) at room temperature The combination of scandium triflate and propargyl α-aryl-α-diazoacetates proved to be efficient catalyst-reagent system for the controlled C-H bond functionalization to afford 1,3-dicarbonyl alkylation products RCH(CH(C(O)R1)2)C(O)OCH2CCH. The protocol uses inexpensive Sc(OTf)3 (5 mol%) and the reaction did not require the use of expensive catalysts or ligands and worked efficiently at room temperature The practicality of the protocol has been demonstrated by the gram scale synthesis.

Tetrahedron Letters published new progress about Alkylation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Recommanded Product: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Denis, Camille published the artcileSynthesis of 3,3-Diarylazetidines by Calcium(II)-Catalyzed Friedel-Crafts Reaction of Azetidinols with Unexpected Cbz Enhanced Reactivity, SDS of cas: 151-10-0, the main research area is diarylazetidines preparation calcium catalyzed Friedel Crafts reaction; alkylation Cbz azetidine phenol intermediate carbocation.

Azetidines are valuable motifs that readily access under explored chem. space for drug discovery. 3,3-Diarylazetidines are prepared in high yield from N-Cbz azetidinols in a calcium(II)-catalyzed Friedel-Crafts alkylation of (hetero)aromatics and phenols, including complex phenols such as β-estradiol. Electron poor phenols undergo O-alkylation. The product azetidines can be derivatized to drug-like compounds through the azetidine nitrogen and the aromatic groups. The N-Cbz group is crucial to reactivity by providing stabilization of an intermediate carbocation on the four-membered ring.

Organic Letters published new progress about Alkylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, SDS of cas: 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem