Category: 151-10-0

Li, Ziyong published the artcileConstruction of C-C Axial Chirality via Asymmetric Carbene Insertion into Arene C-H Bonds, SDS of cas: 151-10-0, the main research area is biaryl atropisomer preparation stereoselective; diazonaphthoquinone aniline arene chiral transfer carbene insertion; C-H insertion; asymmetric catalysis; atropisomer; axial chirality; carbene.

By using diazonaphthoquinones and anilines as key reagents and through a point-to-axis chiral transfer strategy, the atroposelective synthesis via asym. C(sp2)-H bond insertion reaction of arenes has been realized under rhodium catalysis, providing the resulting biaryl atropisomers in moderate to excellent yields with good enantiomeric ratios (up to 99:1). Further elaboration indicates this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.

Angewandte Chemie, International Edition published new progress about Atropisomers. 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

Zheng, Jie published the artcileCascade intramolecular Prins/Friedel-Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols, COA of Formula: C8H10O2, the main research area is aryl tetralinol diastereoselective preparation; acetaldehyde nucleophile Prins Friedel Craft boron trifluoride etherate catalyst; tetrahydrobenzoannulinol aryl diastereoselective preparation; propanal nucleophile Prins Friedel Craft boron trifluoride etherate catalyst; 4-aryltetralin-2-ol; 5-aryl-benzo[7]annulen-7-ol; Prins/Friedel–Crafts; cascade reaction.

The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanal with BF3·Et2O catalyzed intramol. Prins reaction afforded intermediary benzyl carbenium ions, which were then trapped by a variety of electron-rich aromatics via Friedel-Crafts alkylation. This cascade Prins/Friedel-Crafts cyclization protocol paved an expedient path to medicinally useful 4-aryltetralin-2-ol I [R1 = H, OMe, Cl, NO2; R2 = H, Me; R3 = H, Me, Ph; R4 = 2-furyl, 2-thienyl, 3,4-(MeO)2C6H3, etc.] and 5-aryltetrahydro-5H-benzo[7]annulen-7-ol derivatives II [R5 = 2-furyl, 3,4-(MeO)2C6H3].

Beilstein Journal of Organic Chemistry published new progress about Aromatic alcohols Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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

Zhang, Xing-Long published the artcileDehydrogenative β-Arylation of Saturated Aldehydes Using Transient Directing Groups, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is dehydrogenative beta arylation saturated aldehyde transient directing group; diastereoselective cinnamaldehyde preparation cross dehydrogenative coupling aldehyde arene.

An unprecedented cross-dehydrogenative-coupling (CDC) reaction of saturated aldehyde β-C-H with arenes to form cinnamaldehydes via the cleavages of four C-H bonds has been developed. The reaction possesses complete E-stereoselectivity for the C=C double bond. The protocol is featured by atom and step economy, mild reaction conditions, and convenient operation.

Organic Letters published new progress about Aromatic hydrocarbons Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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

Ding, Yao published the artcileRegioselective C-H Amidation of (Alkyl)arenes by Iron(II) Catalysis, COA of Formula: C8H10O2, the main research area is regioselective amidation alkylarene iron catalysis sulfonyl azide nitrogen source; aromatic amine preparation alkylarene amidation.

A nondirected amidation reaction of aromatic C-H bond was developed under iron(II) catalysis, using sulfonyl azides as the nitrogen source. The reaction displayed a broad substrate scope and good regioselectivities in the aspects of aromatic ring vs alkyl chain and different aromatic position of (alkyl)arenes. This method provided a new protocol for the synthesis of some aromatic amines, which were hard to achieve in a previous report.

Organic Letters published new progress about Amidation. 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

Boeldl, Marlene published the artcileDehydrative Coupling of Benzylic Alcohols Catalyzed by Bronsted Acid/Lewis Base, Application In Synthesis of 151-10-0, the main research area is olefin preparation diastereoselective; alc dehydrative coupling sulfonic acid triphenylphosphane catalyst; diaryl ethane preparation regioselective; benzylic alc arene dehydrative hydroarylation Bronsted acid catalyst.

A simple and direct, metal-free protocol for the synthesis of olefins (E)-4-R1-2-R2C6H3CH(Me)CH=CHC6H3-4-R1-2-R2 (R1 = H, Ph, Br, F, I, Cl, NO2, CF3, Me; R2 = H, Cl, Me) by applying catalytic amounts of a sulfonic acid and triphenylphosphane under air has been reported. A variety of olefins could be synthesized from benzylic alcs. 4-R1-2-R2C6H3CH(Me)OH under relatively mild conditions. Addnl., dehydrative hydroarylation of benzylic alcs. ArCH(OH)Me (Ar = 2-chlorophenyl, biphenyl-4-yl, 2-naphthyl, etc.) with electron-rich arenes 3,5-(MeO)2C6H3R3 (R3 = H, OMe) was possible by using only Bronsted acid under otherwise same reaction conditions. Here, it shows that phosphane additives are essential to overcome oligomerization as main side reaction by the occupancy of the reactive carbocation intermediate.

European Journal of Organic Chemistry published new progress about Aralkyl alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Application In Synthesis of 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

La Manna, Pellegrino published the artcileGreen, Mild, and Efficient Friedel-Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions, Category: isoquinoline, the main research area is arene benzyl chloride resorcinarene macrocycle catalyst Friedel Craft benzylation; benzylarene regioselective preparation green chem; alkylation; catalysis; hydrogen bonds; resorcinarenes; supramolecular chemistry.

Metal-free Friedel-Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploited the hydrophobicity of the resorcinarene macrocycle e.g., I. The proposed mechanism was based on the activation of benzyl chloride by H-bonding interactions with catalyst e.g., I. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride led to polarization of the C-Cl bond, which consequently promoted electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene I as catalyst. The FCB of benzene was industrially relevant for the synthesis of diphenylmethane and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst I.

ChemSusChem published new progress about Benzylation catalysts (regioselective). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Khan, Jabir published the artcileSilyl Cation-Initiated, Bronsted Acid-Catalyzed Strategy toward Unsymmetrical 3,3-Disubstituted 2-Oxindoles and Azonazine Cores, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is diaryl oxindole regioselective preparation; keto amide arene Friedel Craft cyclization Bronsted acid catalyst; sulfenylated oxindole derivative regioselective preparation; thiophenol keto amide Friedel Craft cyclization Bronsted acid catalyst; tetracyclic azonazine preparation; oxindole diaryl Friedel Craft cyclization Bronsted acid catalyst.

Herein, a mild, metal-free, robust approach for synthesizing valuable and sterically demanding unsym. 3,3-diaryl 2-oxindoles I [R = Me, Ph; R1 = Ph, 4-MeOC6H4, 4-OH-3-MeC6H4, etc.; R2 = H, Me, Ph, Bn; R3 = H, 5-OMe, 5-Br, etc.] and 3-sulfenylated 2-oxindole derivatives II [R4 = Me, Ph; R5 = nBu, Ph, Bn, etc.; R6 = H, Me, Ph, Bn] via reductive cyclization of α-ketoamides with arenes /thiophenols was reported. This operationally simple protocol was initiated by a silyl cation and further catalyzed by a Bronsted acid. The products were afforded in excellent regioselectivity and good functional group tolerance. Also, ring-closing reaction of compounds I under similar reaction conditions afforded scaffolds of azonazine and its derivatives III [R7 = H, 2-Cl-6-Me; R8 = H, Me, Ph, Bn; R9 = Me, Cl, F; R10 = Me, Ph] with an excellent syn-diastereoselectivity bearing all-carbon quaternary stereocenters.

Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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

Liu, Mingyang published the artcileChlorination of arenes via the degradation of toxic chlorophenols, Formula: C8H10O2, the main research area is arene chlorination toxic chlorophenol degradation; aryl chloride; chlorophenol pollutant; decontamination; isofunctional reaction.

Aryl chlorides are among the most versatile synthetic precursors, and yet inexpensive and benign chlorination techniques to produce them are underdeveloped. Authors propose a process to generate aryl chlorides by chloro-group transfer from chlorophenol pollutants to arenes during their mineralization, catalyzed by Cu(NO3)2/NaNO3 under aerobic conditions. A wide range of arene substrates have been chlorinated using this process. Mechanistic studies show that the Cu catalyst acts in cooperation with NOx species generated from the decomposition of NaNO3 to regulate the formation of chlorine radicals that mediate the chlorination of arenes together with the mineralization of chlorophenol. The selective formation of aryl chlorides with the concomitant degradation of toxic chlorophenol pollutants represents a new approach in environmental pollutant detoxication. A reduction in the use of traditional chlorination reagents provides another (indirect) benefit of this procedure.

Proceedings of the National Academy of Sciences of the United States of America published new progress about Chlorination. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Formula: C8H10O2.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zerov, Aleksey V. published the artcileTfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is trifluoromethyl indane preparation diastereoselective crystal mol structure; diaryl trimethylsilyloxy allyl alc arene cyclization.

The reaction of TMS-ethers of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-ols (E)-RC(CF3)(OTMS)CH=CHR1 (R = Ph, 3,4-dimethoxyphenyl, thiophen-2-yl, etc.; R1 = Ph, 2H-1,3-benzodioxol-5-yl, 4-methoxyphenyl, etc.) with arenes ArH (Ar = Ph, 4-bromophenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,4,6-trimethylphenyl) in TfOH at room temperature for 5 min results in the formation of trans-/cis-1,3-diaryl-1-trifluoromethyl indanes I [R2 = H, 5-Me, 5,6-(MeO)2, etc.] in good yields (up to 99%). The predominant or exclusive formation of indanes I with a trans-configuration of 1,3-diaryl groups has been observed The reaction proceeds through an intermediate formation of the corresponding mesomeric CF3-allyl cations. A plausible reaction mechanism is discussed.

Organic Chemistry Frontiers published new progress about Allylic alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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

Dam, Jean published the artcileCeric Ammonium Sulfate (CAS) Mediated Oxidations of Benzophenones Possessing a Phenolic Substituent for the Synthesis of Xanthones and Related Products, Related Products of isoquinoline, the main research area is xanthone preparation ceric ammonium sulfate oxidation phenolic benzophenone.

Work previously published by our group described novel methodol. for the synthesis of xanthones and related products from phenolic benzophenones in a reaction mediated by ceric ammonium sulfate (CAS). In this paper we further explore this novel reaction by subjecting an addnl. set of phenolic benzophenones to CAS to afford a range of compounds, including xanthones, 9H-xanthen-2,9(4aH)-diones, 3H-spiro[benzofuran-2,1′-cyclohexa[2,5]diene]-3,4′-diones, and biaryl compounds A comparison of these reactions with the more commonly used oxidant ceric ammonium nitrate (CAN) was also conducted. Based on these results, greater insight into the reaction mechanism has been gained. In addition, the conversion of the synthesized xanthen-2,9(4aH)-diones to xanthones by treatment with sodium dithionite is described.

Journal of Organic Chemistry published new progress about Biaryls Role: SPN (Synthetic Preparation), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem