Category: 104-01-8

Li, Zhen published the artcileLigand-Enabled C-H Hydroxylation with Aqueous H2O2 at Room Temperature, Safety of 4-Methoxyphenylacetic acid, the main research area is benzoic phenylacetic acid hydroxylation hydrogen peroxide carboxyl pyridone ligand; carbon hydrogen bond activation palladium catalyst.

With the large number of Pd(II)-catalyzed C-H activation reactions of native substrates developed in the past decade, the development of catalysts to enable the use of green oxidants under safe and practical conditions has become an increasingly important challenge. Notably, the compatibility of Pd(II) catalysts with sustainable aqueous H2O2 has been a long-standing challenge in catalysis including Wacker-type oxidations Authors report herein a bifunctional bidentate carboxyl-pyridone (CarboxPyridone) ligand that enables room-temperature Pd-catalyzed C-H hydroxylation of a broad range of benzoic and phenylacetic acids with an industry-compatible oxidant, aqueous hydrogen peroxide (35% H2O2). The scalability of this methodol. is demonstrated by a 1000 mmol scale reaction of ibuprofen (206 g) using only a 1 mol % Pd catalyst loading. The utility of this protocol is further illustrated through derivatization of the products and synthesis of polyfluorinated natural product coumestan and pterocarpene from phenol intermediates prepared using this methodol.

Journal of the American Chemical Society published new progress about C-H bond activation. 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

Buckley, Aoife M. published the artcileDirhodium Carboxylate Catalysts from 2-Fenchyloxy or 2-Menthyloxy Arylacetic Acids: Enantioselective C-H Insertion, Aromatic Addition and Oxonium Ylide Formation/Rearrangement, Synthetic Route of 104-01-8, the main research area is dirhodium carboxylate preparation; arylacetic acid diazocarbonyl compound addition reaction; tetrahydrothiopyran preparation enantioselective diastereoselective; diazooxosulfone carbon hydrogen insertion rhodium catalyst; Aromatic Addition; Carbenoids; C−H Insertion; Diazo Compounds; Rhodium Catalysis.

A new class of dirhodium carboxylate catalysts I (Ar = Ph, naphthalen-2-yl, 4-bromophenyl, etc.; R = 1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl, menthyl) have been designed and synthesized from 2-fenchyloxy or 2-menthyloxy arylacetic acids ArC(OR)COOH which display excellent enantioselectivity across a range of transformations of α-diazocarbonyl compds ArC(=N2)C(O)Ot-Bu. The catalysts were successfully applied to enantioselective C-H insertion reactions of aryldiazoacetates and α-diazo-β-oxosulfones R1(CH2)4S(O)OC(=N2)C(O)R2 (R1 = Ph, octyl, 4-fluorophenyl, etc.; R2 = Me, Bn, Ph) and Me 2-((cyclohexylethyl)sulfonyl)-2-diazoacetate affording the resp. products II and Me (1R,4aS,8aR)-octahydro-1H-isothiochromene-1-carboxylate 2,2-dioxide in up to 93% ee with excellent trans diastereoselectivity in most cases. Furthermore, efficient desymmetrization in an intramol. C-H insertion was achieved. In addition, these catalysts prove highly enantioselective for intramol. aromatic addition with up to 88% ee, and Me 2-diazo-3-(2-allyloxyphenyl)-3-oxopropionate formation and rearrangement with up to 74% ee.

ChemCatChem published new progress about Diastereoselective synthesis. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Synthetic Route of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kumar, Jogendra published the artcileEnhancing the Extent of Enolization for α-C-H Bonds of Aliphatic Carboxylic Acid Equivalents via Ion Pair Catalysis: Application toward α-Chalcogenation, Related Products of isoquinoline, the main research area is thioether selenoether preparation regioselective; aliphatic carboxamide thiol thiolation potassium phosphate catalyst; diselenide aliphatic carboxamide selenylation potassium phosphate catalyst.

In general, the α-functionalization of carboxylic acid derivatives RCH2C(O)NHR1 [R = Me, n-Bu, Ph, 3-thienyl, etc.; R1 = pyridin-2-yl, 4-Methylpyridin-2-yl, pyrimidin-2-yl, etc.] requires either a transition metal catalyst or a stoichiometric activating agent/strong base/external additive. A transition metal free α-chalcogenation of aliphatic carboxylic acid equivalent was reported via ion pair formation using K3PO4 as a catalyst. Mild conditions, broad scope, scalability of the process, attaining bioactive glucokinase activators, and some synthetic intermediates establish merits of the strategy.

Journal of Organic Chemistry published new progress about C-H bond activation. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zhao, Feng published the artcileEnantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Broensted Acid Catalysis, Product Details of C9H10O3, the main research area is aminoarylpropanoate enantioselective preparation; enantioselective aminomethylation pentafluorophenyl arylacetate isothiourea hydrochloride catalyst; mechanism enantioselective aminomethylation pentafluorophenyl arylacetate acylisothiouronium intermediate; aminomethylation; cooperative catalysis; isothiourea; mechanistic studies; α-aryl-β-amino acid.

The synthesis of α-aryl-β2-amino esters such as (S)-Bn2NCH2CHPhCO2Me (Bn = PhCH2) through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Broensted acid catalysis is demonstrated. The scope and limitations of this process are explored (25 examples, up to 94% yield and 96:4 er), and the method was applied to the syntheses of (S)-venlafaxine hydrochloride and (S)-nakinadine B. Mechanistic studies are consistent with a C(1)-ammonium enolate pathway being followed rather than an alternative dynamic kinetic resolution process. Control studies indicate that (i) a linear effect between catalyst and product er is observed; (ii) an acyl ammonium ion can be used as a precatalyst; (iii) reversible isothiourea addition to an in situ generated iminium ion leads to an off-cycle intermediate that can be used as a productive precatalyst.

Angewandte Chemie, International Edition published new progress about Aminomethylation (stereoselective). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Product Details of C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Wu, Wen-Biao published the artcileConstructing tertiary alcohols with vicinal stereocenters: highly diastereo- and enantioselective cyanosilylation of α-branched acyclic ketones and their kinetic resolution, Name: 4-Methoxyphenylacetic acid, the main research area is tertiary alc preparation diastereoselective enantioselective; alpha branched acyclic ketone cyanosilylation.

Highly diastereo- and enantioselective C-C bond-forming reaction of racemic α-branched ketones to construct tertiary alcs. with adjacent stereocenters was reported. Accordingly, a highly stereoselective cyanosilylation of racemic ketones was developed using bifunctional cyanating reagent, Me2(CH2Cl)SiCN, giving Cα-tetrasubstituted silyl cyanohydrins with two vicinal stereocenters in up to >20:1 diastereomeric ratio (dr) and 90-98% enantiomeric excess (ee) values, which could underwent various diversification reactions by manipulating the chloromethyl group. A highly selective kinetic resolution of acyclic α-branched ketones was also developed that allowed facile access to acyclic α-alkyl, allyl, and propargyl ketones with good recovery and excellent ee values. The synthetic value of this protocol was further demonstrated by the formal synthesis of the anti-obesity agent, taranabant (MK-0364). The activation of Jacobsen’s privileged catalyst (salen)AlCl by a suitable phosphorane played a crucial role in the reaction. X-Ray crystallog. anal. of single crystals of phosphorane-(salen)AlCl complexes and theor. calculations helped to provide a working model. The present transformation opened a new path for the catalytic stereoselective synthesis of stereochem. complex tertiary alcs. featuring two stereocenters (adjacent or not) from racemic ketones.

CCS Chemistry published new progress about Carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Name: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Pham, Hang T. published the artcileSynthesis of 2-Arylbenzothiazol-5-amines from N,N-Dialkyl-3-nitroanilines, Category: isoquinoline, the main research area is arylbenzothiazolamine preparation DABCO base; dialkylnitroarene sulfur methylazaarene arylacetic acid cyclization multicomponent reaction.

A simple method for coupling of N, N-dialkyl-3-nitroarenes, I (R1 = Me2N, morpholinyl, 4-Me-piperazinyl,etc.) elemental sulfur, and activated sp3 C-H bonds in 2-methylazaarenes or arylacetic acids to afford derivatives of 2-arylbenzothiazol-5-amines II (R2 = Ph, 4-MeC6H4, 2-pyridinyl, 2-thiphenyl, etc. ) is described. Only DABCO base was required, and many heterocycles such as imidazoles, oxazoles, quinolines, and thiophenes were compatible with the reaction conditions. Authors’ approach offers a simple route to useful substituted thiazol-5-amines from com. available nitroarenes.

Synlett published new progress about Benzothiazoles Role: SPN (Synthetic Preparation), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yang, Xinyue published the artcileA Mild Method for Access to α-Substituted Dithiomalonates through C-Thiocarbonylation of Thioester: Synthesis of Mesoionic Insecticides, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is alpha substituted dithiomalonate preparation; thioester imidazole carbothioate thiocarbonylation.

An efficient method for targeting a variety of sym. and asym. αsubstituted dithiomalonates (DTMs) RSC(O)C(R1R2)C(O)SEt [R = Et, i-Pr, t-Bu, Bn, 4-MeC6H4; R1 = H, Me, Ph; R2 = Et, Ph, 4-FC6H4, etc.] was described, utilizing 1H-imidazole-1-carbothioates as reactive acylating agents and MgBr2·OEt2/DBU or LiHMDS for soft or hard enolization conditions of thioesters, resp. The utility of this methodol. was demonstrated through the synthesis of the pyridopyrimidine mesoionic insecticides: triflumezopyrim and dicloromezotiaz.

Advanced Synthesis & Catalysis published new progress about Enolization. 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

Harnedy, James published the artcileElectrochemical oxidative Z-selective C(sp2)-H chlorination of acrylamides, Safety of 4-Methoxyphenylacetic acid, the main research area is propenamide magnesium chloride chemoselective diastereoselective electrochem oxidation chlorination; chloropropenamide preparation.

An electrochem. method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides was developed. This catalyst and organic oxidant free method was applicable across various substituted tertiary acrylamides and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochem. process was performed on gram scale in flow.

Chemical Communications (Cambridge, United Kingdom) published new progress about Chemoselectivity. 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

Shibata, Takanori published the artcileEnantioselective Cross-Coupling of Electron-Deficient Alkenes via Ir-Catalyzed Vinylic sp2 C-H Alkylation, Category: isoquinoline, the main research area is alkenyl amide acrylate iridium catalyst enantioselective regioselective cross coupling; carboxy alkenylamide preparation.

A chiral Ir-catalyzed reaction of α-aryl-α,β-unsaturated amides with β-substituted acrylates proceeded to give formal conjugate adducts in high yield and ee (up to 99% yield and up to 95% ee). This was the first example of the enantioselective cross-coupling of two different electron-deficient alkenes via vinylic sp2 C-H activation, and polyfunctionalized chiral compounds were obtained.

Organic Letters published new progress about Pyrrolidines Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kong, Duanyang published the artcileFast Carbon Isotope Exchange of Carboxylic Acids Enabled by Organic Photoredox Catalysis, Product Details of C9H10O3, the main research area is carbon labeled carboxylic acid preparation; carboxylic acid carbon isotope exchange photoredox catalyst.

Carbazole/cyanobenzene photocatalysts I (R = 9H-carbazol-9-yl; R1 = CN, PhCH2) promoted the direct isotopic carboxylate exchange of a wide variety of C(sp3) carboxylic acids with 13CO2. Substrates that are not compatible with transition-metal-catalyzed degradation-reconstruction approaches or prone to thermally induced reversible decarboxylation undergo isotopic incorporation at room temperature in short reaction times. The radiolabeling of drug mols. and precursors with [11C]CO2 is also demonstrated.

Journal of the American Chemical Society published new progress about Carbazoles Role: CAT (Catalyst Use), RCT (Reactant), SPN (Synthetic Preparation), USES (Uses), RACT (Reactant or Reagent), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Product Details of C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem