Category: 93-04-9

Shi, Tiancai published the artcileMatrix effect compensation for analyte protectants during aroma component analysis of tobacco, Application of 2-Methoxynaphthalene, the publication is Yancao Keji (2021), 54(9), 27-39, database is CAplus.

In order to solve the challenge that strong polar analyte protectants are not well performed in weak polar solvent systems, the solution of acetonitrile:dichloromethane = 2:1 (V/V) was chosen as weak polarity solvent system. The effects of 23 compounds as analyte protectants on the heights and shapes of chromatog. peaks of 31 aroma components were investigated. The chromatog. peaks of the aroma components in solvent added with these analyte protectants were compared with those in tobacco matrix. After optimizing the type, composition and concentration of the protectants, a suitable combination of analyte protectants was developed. In addition, 15 aroma components in tobacco (other than the 31 aroma components mentioned above) were chosen to verify the matrix compensation effect of the developed analyte protectant combination. The results showed that the suitable analyte protectants combination was malic acid (1000 mg/L) + 1,2-tetradecanediol (1000 mg/L). By adding the optimized analyte protectants combination into the solvent standard solution, a satisfactory matrix compensation effect was achieved. The linearity of the calibration curve for each aroma component was greatly improved, and the slope and linear correlation coefficient (r²) were basically consistent with the matrix-matched calibration curve. The matrix effect of aroma components in tobacco during GC/MS anal. was compensated by adding analyte protectants.

Yancao Keji published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10N4, Application of 2-Methoxynaphthalene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Misal, Balu published the artcileSulfated polyborate-H₂O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes, Formula: C11H10O, the publication is Tetrahedron Letters (2021), 153154, database is CAplus.

Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogeneous conditions, iodination protocol of arenes was developed, which can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activated N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tuned sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chems., API and natural products.

Tetrahedron Letters published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Formula: C11H10O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Dalai, Pallaba Ganjan published the artcileGeneration of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C-H Halogenation, Application In Synthesis of 93-04-9, the publication is Advanced Synthesis & Catalysis (2022), 364(5), 1031-1038, database is CAplus.

A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and DMSO (DMSO) for C-H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur ylide, which undergoes pyrolytic elimination of ethylene by affording halonium ions. These ions were accumulated and stabilized by DMSO through coordination by forming halogen cation pools for the halogenation reaction. This protocol was selective for electrophilic monohalogenation of arenes at room temperature; however, polyhalogenated products were formed by raising the reaction temperature Late-stage halogenation of heteroarenes and some commonly marketed drugs signifies the synthetic utility of this protocol in pharmaceutical chem. Unlike the classical methods, the in-situ generated electrophilic bromonium ion was further exploited for the direct synthesis of α-diketones from the alkenes under base-free conditions.

Advanced Synthesis & Catalysis published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Application In Synthesis of 93-04-9.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Li, Guolin published the artcileTransition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond, Recommanded Product: 2-Methoxynaphthalene, the publication is Nature Communications (2020), 11(1), 2890, database is CAplus and MEDLINE.

A transition-metal-free cross-coupling strategy utilizing aryl(heteroaryl) Me sulfoxides R¹S(O)Me (R¹ = Ph, 4-NCC₆H₄, 2-naphthyl, 3-pyridyl, 2-benzimidazolyl, etc.) and alcs. R²OH (R² = Me, i-Pr, 2-cyclohexylethyl, 1-adamantylmethyl, etc.) to afford alkyl aryl(heteroaryl) ethers R¹OR² is reported. Two drug mols. were successfully prepared using this protocol as a key step and emphasized its potential utility in medicinal chem. A DFT computational study suggests that the reaction proceeds via initial addition of the alkoxide to the sulfoxide. This adduct facilitates further intramol. addition of the alkoxide to the aromatic ring wherein charge on the aromatic system is stabilized by the nearby potassium cation. Rate-determining fragmentation then delivers Me sulfenate and the aryl or heteroaryl ether. This study establishes the feasibility of nucleophilic addition to an appended sulfoxide as a means to form a bond to aryl(heteroaryl) systems and this modality is expected to find use with many other electrophiles and nucleophiles leading to new cross-coupling processes.

Nature Communications published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Recommanded Product: 2-Methoxynaphthalene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kurose, Ryo published the artcileMetal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst, Synthetic Route of 93-04-9, the publication is Organic Letters (2021), 23(6), 2380-2385, database is CAplus and MEDLINE.

Herein we report an efficient synthetic method for the electrophilic trifluoromethylthiolation of aromatic compounds The key is to use triptycenyl sulfide (Trip-SMe) and TfOH to enhance the electrophilicity of SCF₃ fragment through the formation of sulfonium intermediates. This method enables direct installation of an SCF₃ group onto unactivated aromatics at room temperature, adopting a com. available saccharin-based reagent. Preliminary DFT calculation was carried out to investigate the substitution effect on the catalytic activity.

Organic Letters published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Synthetic Route of 93-04-9.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

McClain, Edward J. published the artcileDesign and implementation of a catalytic electron donor-acceptor complex platform for radical trifluoromethylation and alkylation, Synthetic Route of 93-04-9, the publication is ACS Catalysis (2020), 10(21), 12636-12641, database is CAplus.

Electron donor-acceptor (EDA) complexes can controllably generate radicals under mild conditions through selective photoexcitation events. However, unproductive reactivity from fast deactivation of the photoexcited complexes through back electron transfer has slowed the development of EDA complexes in synthetic methodol. Here, we disclose the study of EDA complexes derived from 2-methoxynaphthalene donor and acylated Et isonicotinate N-oxide acceptor that undergo a fast N-O bond fragmentation event upon photoexcitation. This reaction design not only overcomes the limitations of back electron transfer but also enables regeneration of the donor species, representing a rare example of EDA photochem. in a catalytic regime. The synthetic utility is demonstrated through visible light-driven radical trifluoromethylation and Minisci alkylation reactions. The scalability of the EDA complex-promoted reaction is evidenced by the successful multigram-scale trifluoromethylation of Me N-Boc pyrrole-2-carboxylate in a continuous flow manifold.

ACS Catalysis published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Synthetic Route of 93-04-9.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Toupalas, Georgios published the artcileNon-innocent electrophiles unlock exogenous base-free coupling reactions, Application of 2-Methoxynaphthalene, the publication is Nature Catalysis (2022), 5(4), 324-331, database is CAplus.

Introduced a unifying strategy that eliminates the need for an exogenous base through the use of non-innocent electrophiles (NIE), which were equipped with a masked base that was released in a controlled fashion during the reaction. The universal applicability of this concept were demonstrated by turning multiple, traditionally base-dependent, catalytic reactions into exogenous base-free homogeneous processes. Furthermore, the advantageous features of NIEs were demonstrated in multiple applications, such as in a micromole-scale fluorescence-based assay. This led to the discovery of a Ni-catalyzed deoxygenation reaction of aryl carbamates using isopropanol as a benign reductant. In a broader context, this work provided a conceptual blueprint for the strategic utilization of NIEs in catalysis.

Nature Catalysis published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C8H5F3O3, Application of 2-Methoxynaphthalene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Lamola, Jairus L. published the artcileEvaluation of P-bridged biaryl phosphine ligands in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, Product Details of C11H10O, the publication is RSC Advances (2021), 11(43), 26883-26891, database is CAplus and MEDLINE.

A family of biaryl phosphacyclic ligands derived from phobane and phosphatrioxa-adamantane frameworks was described. The rigid biaryl phosphacycles were efficient for synthesis of biaryls ArAr¹ [Ar = 3-MeC₆H₄, 2-naphthyl, 2-thienyl, etc.; Ar¹ = Ph, 2-MeC₆H₄, 2,6-di-MeC₆H₃] via palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl bromides/chlorides with phenylboronic acids. In particular, coupling reactions of the challenging sterically hindered and heterocyclic substrates were viable at room temperature

RSC Advances published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Product Details of C11H10O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Palav, Amey published the artcileNCBSI/KI: A Reagent System for Iodination of Aromatics through In Situ Generation of I-Cl, Application In Synthesis of 93-04-9, the publication is Journal of Organic Chemistry (2021), 86(17), 12467-12474, database is CAplus and MEDLINE.

In-situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system was developed. The NCBSI reagent required no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge d. on nitrogen. The system was adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide was recovered and transformed to NCBSI and made the protocol eco-friendly and cost-effective.

Journal of Organic Chemistry published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Application In Synthesis of 93-04-9.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Dao, Pham Duy Quang published the artcileSynthesis of Trinuclear Benzimidazole-Fused Hybrid Scaffolds by Transition Metal-Free Tandem C(sp²)-N Bond Formation under Microwave Irradiation, Application of 2-Methoxynaphthalene, the publication is European Journal of Organic Chemistry (2021), 2021(29), 4088-4098, database is CAplus.

The compounds 2-(2-bromoaryl)benzimidazoles e.g., 2-(2-bromocyclohex-1-en-1-yl)-1H-1,3-benzodiazole and 2-(2-bromovinyl)benzimidazoles e.g., 2-[(1Z)-1-bromo-1-phenylprop-1-en-2-yl]-1H-1,3-benzodiazole have been coupled and cyclized with 2-methoxybenzimidazoles e.g., 2-methoxy-1H-1,3-benzodiazole and 2-aryloxybenzimidazoles e.g., 2-methoxy-1H-naphtho[2,3-d]imidazole as building blocks in the presence of a base under microwave irradiation to give a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]quinazolines e.g., I and benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]pyrimidines e.g., II, resp., in good yields. The compounds 2-(2-bromoaryl)imidazoles e.g., 2-(2-bromocyclohex-1-en-1-yl)-4,5-diphenyl-1H-imidazole and 2-(2-bromovinyl)imidazoles e.g., (Z)-2-(1-bromo-1-phenylprop-1-en-2-yl)-4,5-diphenyl-1H-imidazole also reacted with 2-methoxybenzimidazoles (e.g., 2-methoxy-1H-1,3-benzodiazole/e.g., 2-methoxy-1H-naphtho[2,3-d]imidazole) in the presence of base under microwave irradiation to give a class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]quinazolines e.g., III and benzo[4,5]imidazo[1,2-a]imidazo[1,2-c]pyrimidines e.g., IV, resp., in similar yields. This process seems to proceed via an initial C(sp²)-N coupling by an addition-elimination nucleophilic aromatic substitution (S_NAr) and subsequent cyclization accompanied by extrusion of alcs.

European Journal of Organic Chemistry published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Application of 2-Methoxynaphthalene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem