Category: 1993/4/9

Li, Laiqiang published the artcileSite-Selective Electrochemical C-H Cyanation of Indoles, Name: 2-Methoxynaphthalene, the publication is Organic Letters (2021), 23(15), 5983-5987, database is CAplus and MEDLINE.

An electrochem. approach for the site-selective C-H cyanation of indoles to form indole-carbonitriles I [R¹ = CN, Ph; R² = Me, CN, C(O)OMe, etc.; R³ = H, 4-Me, 5-F, 6-Cl, etc.; R⁴ = Me, Bn, i-Pr, etc.] employing readily available TMSCN as cyano source has been developed. The electrosynthesis relied on the tris(4-bromophenyl)amine as a redox catalyst, which achieved better yield and regioselectivity. A variety of C2- and C3-cyanated indoles were obtained in satisfactory yields. The reactions were conducted in a simple undivided cell at room temperature and obviated the need for transition-metal reagent and chem. oxidant.

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, Name: 2-Methoxynaphthalene.

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

Hong Nguyen, Thi Anh published the artcileMetal-free, Direct Acetoxylation of Arenes, HPLC of Formula: 93-04-9, the publication is Organic Letters (2021), 23(21), 8127-8131, database is CAplus and MEDLINE.

A metal-free, direct acetoxylation reaction using sodium nitrate under an anhydrous environment of trifluoroacetic acid, acetic acid and acetic anhydride was reported. Arenes (31 examples), with oxidation potentials (E_ox, in V vs SCE) lower than benzene (2.48 V), were acetoxylated with good yields and regioselectivity. A stepwise, single electron-transfer mechanism was proposed.

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, HPLC of Formula: 93-04-9.

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

Wang, Tao published the artcileA Metal-Free Direct Arene C-H Amination, Recommanded Product: 2-Methoxynaphthalene, the publication is Advanced Synthesis & Catalysis (2021), 363(11), 2783-2795, database is CAplus.

Here, a metal-free arene e.g., mesitylene C-H amination using hydroxylamine derivatives 4-(CH₃)C₆H₅S(O)₂ON(R)R¹ (R = H, Me; R¹ = Me, Boc, Bn, etc.) under benign conditions was reported. A charge transfer interaction between the aminating reagents and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven exptl. In addition, this was rationalized by a theor. study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen mol.

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 C10H14BNO4S, Recommanded Product: 2-Methoxynaphthalene.

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

Rawat, Vishal Kumar published the artcileNickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant, HPLC of Formula: 93-04-9, the publication is Synthesis (2021), 53(18), 3397-3403, database is CAplus.

Nickel-catalyzed reductive homocoupling of aryl ethers has been achieved with Mg(anthracene)(thf)₃ as a readily available low-cost reductant. DFT calculations provided a rationale for the specific efficiency of the diorganomagnesium-type two-electron reducing agent. The calculations show that the dianionic anthracene-9,10-diyl ligand reduces the two aryl ether substrates, resulting in the homocoupling reaction through supply of electrons to the Ni-Mg bimetallic system to form organomagnesium nickel(0)-ate complexes, which cause two sequential C-O bond cleavage reactions. The calculations also showed cooperative actions of Lewis acidic magnesium atoms and electron-rich nickel atoms in the C-O cleavage reactions.

Synthesis 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, HPLC of Formula: 93-04-9.

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

Borys, Andryj M. published the artcileThe Anionic Pathway in the Nickel-Catalysed Cross-Coupling of Aryl Ethers, Quality Control of 93-04-9, the publication is Angewandte Chemie, International Edition (2021), 60(46), 24659-24667, database is CAplus and MEDLINE.

The Ni-catalyzed cross-coupling of aryl ethers is a powerful method to forge new C-C and C-heteroatom bonds. However, the inert C(sp²)-O bond means that a canonical mechanism that relies on the oxidative addition of the aryl ether to a Ni⁰ center is thermodynamically and kinetically unfavorable, which suggests that alternative mechanisms may be involved. Here, we provide spectroscopic and structural insights into the anionic pathway, which relies on the formation of electron-rich hetero-bimetallic nickelates by adding organometallic nucleophiles to a Ni⁰ center. Assessing the rich co-complexation chem. between Ni(COD)₂ and PhLi has led to the structures and solution-state chem. of a diverse family of catalytically competent lithium nickelates being unveiled. In addition, we demonstrate dramatic solvent and donor effects, which suggest that the cooperative activation of the aryl ether substrate by Ni⁰-ate complexes plays a key role in the catalytic cycle.

Angewandte Chemie, International Edition 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, Quality Control of 93-04-9.

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

Gelis, Coralie published the artcileCatalytic Transfer Hydrogenation of Arenes and Heteroarenes, Category: ethers-buliding-blocks, the publication is Chemistry – A European Journal (2020), 26(62), 14090-14094, database is CAplus and MEDLINE.

Transfer hydrogenation reactions are of great interest to reduce diverse mols. under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy barrier required to dearomatize these compounds In this context, a catalytic transfer hydrogenation reaction for the reduction of benzene derivatives and heteroarenes to form complex 3-dimensional scaffolds bearing various functional groups at room temperature without needing compressed hydrogen gas has been developed.

Chemistry – A European Journal 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, Category: ethers-buliding-blocks.

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

Shigeno, Masanori published the artcileOrganic superbase t-Bu-P4-catalyzed demethylations of methoxyarenes, Application In Synthesis of 93-04-9, the publication is Organic Chemistry Frontiers (2022), 9(14), 3656-3663, database is CAplus.

The organic superbase t-Bu-P4 catalyzes the demethylation reactions of methoxyarenes ROMe [R = 4-cyanophenyl, 1-oxo-2,3-dihydro-1H-inden-5-yl, 1-benzothiophen-5-yl, etc.] in the presence of alkanethiol and hexamethyldisilazane was reported. The system can efficiently convert a variety of substrates, including electron-deficient, -neutral, and -rich substrates and heteroaromatic substrates, and displays excellent functional group tolerance. Computational studies show that the high reactivity achieved by t-Bu-P4 is due to the formation of the nucleophilic naked thiolate species.

Organic Chemistry Frontiers 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 C14H10O4, Application In Synthesis of 93-04-9.

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

Seki, Rin published the artcileSelective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex, Recommanded Product: 2-Methoxynaphthalene, the publication is Journal of the American Chemical Society (2021), 143(17), 6388-6394, database is CAplus and MEDLINE.

We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.

Journal of the American Chemical Society 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 C16H14O6, Recommanded Product: 2-Methoxynaphthalene.

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

Xia, Cencen published the artcileVisible-Light-Mediated Direct Amidation of Arenes and Heteroarenes with N -Aminopyridinium Salts, Application of 2-Methoxynaphthalene, the publication is Synlett, database is CAplus.

A novel photoinduced strategy has been developed for the C-H amidation of aromatics and heteroaromatics by using benzamide radicals such as 1,3,5-trimethylbenzene, 1-methoxynaphthalene, 1-methyl-1H-indole, 1-methyl-1H-pyrrole, etc. with free NH groups generated from N-amidopyridinium salts such as as 1-benzamido-2,4,6-triphenylpyridin-1-ium tetrafluoroborate under visible-light irradiation The new mode of activation of N-amidopyridinium salts proceeds efficiently under mild conditions to give various benzamide derivatives RNHC(O)C₆H₅ (R = 2,4,6-trimethylphenyl, 1-methoxynaphthalen-2-yl, 1-methyl-1H-indol-3-yl, etc.) with free NH groups. In addition, oxazoline analogs, synthesized by the reaction with styrene, demonstrate a substantial range of prospective applications for this versatile protocol.

Synlett 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 C5H5NO3S, Application of 2-Methoxynaphthalene.

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

Liu, Cuibo published the artcileElectrocatalytic Deuteration of Halides with D₂O as the Deuterium Source over a Copper Nanowire Arrays Cathode, Safety of 2-Methoxynaphthalene, the publication is Angewandte Chemie, International Edition (2020), 59(42), 18527-18531, database is CAplus and MEDLINE.

Precise D incorporation with controllable deuterated sites is extremely desirable. Here, a facile and efficient electrocatalytic deuterodehalogenation of halides using D₂O as the deuteration reagent and Cu nanowire arrays (Cu NWAs) electrochem. formed in situ as the cathode was demonstrated. A cross-coupling of C and D free radicals might be involved for this ipso-selective deuteration. This method exhibited excellent chemoselectivity and high compatibility with the easily reducible functional groups (C=C, C C, C=O, C=N, C N). The C-H to C-D transformations were achieved with high yields and D ratios through a 1-pot halogenation-deuterodehalogenation process. Efficient deuteration of less-active bromide substrates, specific D incorporation into top-selling pharmaceuticals, and oxidant-free paired anodic synthesis of high-value chems. with low energy input highlighted the potential practicality.

Angewandte Chemie, International Edition 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, Safety of 2-Methoxynaphthalene.

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