Category: 104-01-8

Du, Xiaoyong published the artcileEnantioselective Hydrogenation of Tetrasubstituted α,β-Unsaturated Carboxylic Acids Enabled by Cobalt(II) Catalysis: Scope and Mechanistic Insights, Computed Properties of 104-01-8, the main research area is arylcycloalkanecarboxylate diastereoselective enantioselective preparation; isopropylarylacetate enantioselective preparation; cobalt catalyst stereoselective hydrogenation tetrasubstituted unsaturated carboxylic acid; transition state structure free energy enantioselective hydrogenation alkenoic acid; DFT calculations; cobalt; mechanisms; tetrasubstituted unsaturated carboxylic acids.

Chiral carboxylic acids are important compounds because of their prevalence in pharmaceuticals, natural products and agrochems. Asym. hydrogenation of α,β-unsaturated carboxylic acids has been widely recognized as one of the most efficient synthetic approaches to afford such compounds Although related asym. hydrogenation of di- and trisubstituted unsaturated acids with noble metals is well established, asym. hydrogenation of challenging tetrasubstituted α,β-unsaturated carboxylic acids is rarely reported. We demonstrate enantioselective hydrogenation of cyclic (2-aryl-1-cycloalkene-1-carboxylic acids) and acyclic (α-isopropylidenearylacetic acids) tetrasubstituted α,β-unsaturated carboxylic acids via cobalt(II) catalysis. This protocol showed broad substrate scope and gave chiral carboxylic acids in good yields with excellent enantiocontrol (up to 98% yield and 99% ee). Combined exptl. and computational mechanistic studies support a CoII catalytic cycle involving migratory insertion and σ-bond metathesis processes. DFT calculations reveal that enantioselectivity may originate from the steric effect between the Ph groups of the ligand and the substrate.

Angewandte Chemie, International Edition published new progress about Carboxylic acids Role: SPN (Synthetic Preparation), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Computed Properties of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Tao, Lei published the artcileSynthesis of Carboxylic Acids, Esters, and Amides from 1,1-Dibromoalkenes via Oxidation of Alkynyl Boronate Intermediates, Synthetic Route of 104-01-8, the main research area is carboxylic acid preparation; dibromoalkene oxone Corey Fuchs reaction oxidation; ester preparation; alc oxone dibromoalkene Corey Fuchs reaction oxidation; amide preparation; amine oxone dibromoalkene Corey Fuchs reaction oxidation.

An efficient and practical method for the synthesis of carboxylic acids RCH2COOH (R = cyclohexyl, biphenyl-4-yl, thiophen-2-yl, etc.), esters RCH2C(O)OR1 (R1 = Me, Bn, cyclopropylmethyl, etc.), and amides RCH2C(O)NR2R3 [R2 = H, Et, i-Pr, Cy, Bn; R3 = n-Bu, cycloproyl, t-Bu, Et, i-Pr, Cy, Bn; R2R3 = -(CH2)2O(CH2)2-] from 1,1-dibromoalkenes RCH=CBr2Me has been developed. The reactions proceed through a key process, the C(sp)-B bond oxidation of alkynyl boronate intermediates with Oxone. This protocol features broad substrate scope, good efficiency, and good functional group compatibility. Moreover, the synthetic practicability was demonstrated by easy gram-scale preparation and the synthesis of drug mols., e.g., diclofenac.

ChemistrySelect published new progress about Aliphatic acids Role: SPN (Synthetic Preparation), PREP (Preparation). 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

Shao, Wen published the artcileNi-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp3) Nucleophiles, HPLC of Formula: 104-01-8, the main research area is nickel catalyzed regiodivergent stereoselective hydroalkylation branched diene unstabilized nucleophile.

Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed, enabling construction of two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display a broad scope, and show excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of postcatalytic modifications.

Journal of the American Chemical Society published new progress about Alkadienes Role: RCT (Reactant), RACT (Reactant or Reagent) (branched). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, HPLC of Formula: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Li, Yuqiang published the artcileReaction scope and mechanistic insights of nickel-catalyzed migratory Suzuki-Miyaura cross-coupling, HPLC of Formula: 104-01-8, the main research area is diarylalkane allylbenzene derivative preparation nickel catalyst; alkyl electrophile aryl vinyl boronic acid Suzuki Miyaura coupling.

In this work, a Ni-catalyzed migratory Suzuki-Miyaura cross-coupling featuring high benzylic or allylic selectivity has been developed. With this method, unactivated alkyl electrophiles and aryl or vinyl boronic acids can be efficiently transferred to diarylalkane or allylbenzene derivatives under mild conditions. Importantly, unactivated alkyl chlorides can also be successfully used as the coupling partners. To demonstrate the applicability of this method, showcase that this strategy can serve as a platform for the synthesis of terminal, partially deuterium-labeled mols. from readily accessible starting materials. Exptl. studies suggest that migratory cross-coupling products are generated from Ni(0/II) catalytic cycle. Theor. calculations indicate that the chain-walking occurs at a neutral nickel complex rather than a cationic one. In addition, the original-site cross-coupling products can be obtained by alternating the ligand, wherein the formation of the products has been rationalized by a radical chain process.

Nature Communications published new progress about Alkanes Role: SPN (Synthetic Preparation), PREP (Preparation) (diaryl). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, HPLC of Formula: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Garcia-Urricelqui, Ane published the artcilesyn-Selective Michael Reaction of α-Branched Aryl Acetaldehydes with Nitroolefins Promoted by Squaric Amino Acid Derived Bifunctional Broensted Bases, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is stereoselective Michael aryl acetaldehyde nitroolefin bifunctional cinchona squaric peptide.

Here we describe a direct access to 2,2,3-trisubstituted syn γ-nitroaldehydes by addition of α-branched aryl acetaldehydes to nitroolefins promoted by a cinchona based squaric acid-derived amino acid peptide. Different α-Me arylacetaldehydes react with β-aromatic and β-alkyl nitroolefins to afford the Michael adducts in high enantioselectivity and syn-selectivity. NMR experiments and DFT calculations predict the reaction to occur through the intermediacy of E-enolate. The interaction between the substrates and the catalyst follows Papai’s model, wherein an intramol. H-bond interaction in the catalyst between the NH group of one of the tert-leucines and the squaramide oxygen seems to be key for discrimination of the corresponding reaction transition states. Thus, e.g., 2-phenylpropanal + (E)-4-chloro-β-nitrostyrene → I (84%, 95:5 dr, 94% ee).

European Journal of Organic Chemistry published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation) (γ-nitro). 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

Schulz, Goeran published the artcileMetal free decarboxylative aminoxylation of carboxylic acids using a biphasic solvent system, Application of 4-Methoxyphenylacetic acid, the main research area is aromatic carboxylic acid aminoxyl radical decarboxylative aminoxylation; alkoxyamine preparation.

The smooth oxidative radical decarboxylation of carboxylic acids with TEMPO and other derivatives as radical scavengers was reported. The key to success was the use of a two-phase solvent system to avoid otherwise predominant side reactions such as the oxidation of TEMPO by persulfate and enabled the selective formation of synthetically useful alkoxyamines. The method does not require transition metals and was successfully used in a new synthetic approach for the antidepressant indatraline.

Organic & Biomolecular Chemistry published new progress about Alkoxylated amines Role: SPN (Synthetic Preparation), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Prabhala, Pavankumar published the artcileFacile one-pot synthetic access to libraries of diversely substituted 3-aryl (Alkyl)-coumarins using ionic liquid (IL) or conventional base/solvent, and an IL-mediated approach to novel coumarin-bearing diaryl-ethynes, Quality Control of 104-01-8, the main research area is aryl alkyl coumarin preparation; acetic acid aryl salicylaldehyde heterocyclization; coumarin diaryl ethyne preparation; arylethyne haloaryl coumarin Sonogashira reaction.

The in-situ formed carbonylimidazole derivatives of R1CH2COOH (R1 = CH3, 4-bromophenyl, naphthalen-1-yl, 3,4,5-trimethoxyphenyl, etc.) react at r.t. with substituted salicylaldehydes R2-2-OHC6H3CHO (R2 = H, 5-OMe, 4-Cl, 5-Br, etc.) in [BMIM][PF6] or [BMIM][BF4] as solvent, and [PAIM][NTf2] as basic-IL, to produce libraries of 3-aryl(alkyl)coumarins I (R2 = H, 6-OMe, 7-Cl, 6-Br, etc.). Whereas these reactions can also be performed with similar efficiency in THF by employing DBU and the IL approach offers easier work-up and recycling of the IL solvent. An IL-mediated approach to the synthesis of novel coumarin-bearing diaryl-ethynes II (R2 = H, 6-OMe; R3 = H, Me, CN, OMe, etc.) and III (R4 = N(CH3)2, CN) by the Sonogashira reaction is also reported, and the potential for recycling/reuse of the IL solvent is shown.

Tetrahedron Letters published new progress about Aliphatic acids Role: RCT (Reactant), RACT (Reactant or Reagent) (aryl). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Quality Control of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Xing, Ai-Ping published the artcileCuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source, Application of 4-Methoxyphenylacetic acid, the main research area is aromatic nitrile preparation; arylacetic acid cyanation copper catalyst.

CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles ArCN [Ar = Ph, 2-MeC6H4, 1-naphthyl, etc.] with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C≡N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.

Catalysis Communications published new progress about Aromatic nitriles Role: SPN (Synthetic Preparation), PREP (Preparation). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Chang, Meng-Yang published the artcileSynthesis of 1-Aryl Isoquinolinones or o-Diaryl Pyrimidines via Bismuth Triflate-Mediated Intermolecular Annulation of Arylacetic Acids with Nitroarylaldehydes or Trimethoxybenzene in the Presence of Acetonitrile, Synthetic Route of 104-01-8, the main research area is aryl isoquinolinone diaryl pyrimidine preparation; nitroarylaldehyde arylacetic acid trimethoxybenzene intermol multicomponent condensation bismuth triflate.

In this article, bismuth triflate (Bi(OTf)3)-controlled intermol. multi-component condensation of oxygenated arylacetic acids with electron-withdrawing nitroarylaldehydes or electron-donating trimethoxybenzene provide 1-aryl isoquinolinones or o-diaryl pyrimidines in acetonitrile at 60°C. The uses of various metal triflates and reaction conditions are investigated in the one-pot reaction. Only water is generated as the byproduct via (4C+1C+1N) and (2C+1N1C+1N1C) annulation routes. Plausible mechanisms have been proposed.

Advanced Synthesis & Catalysis published new progress about Aryl aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent) (nitro). 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

Yu, Lu published the artcileRegio- and Enantioselective Formal Hydroamination of Enamines for the Synthesis of 1,2-Diamines, Product Details of C9H10O3, the main research area is regioselective enantioselective hydroamination enamine diamine synthesis; amines; copper; enamines; enantioselectivity; hydroamination.

The asym. formal hydroamination of enamines using a CuH catalyst is reported [e.g., enamine I + O-acylhydroxylamine II → diamine III (69%, 97:3 e.r.) in presence of (MeO)2MeSiH as hydride source, Cu(OAc)2 and (R)-DTBM-SEGPHOS]. The method provides a straightforward and efficient approach to the synthesis of chiral 1,2-dialkyl amines in good yields with high levels of enantioselectivities for a broad range of substrates, and should have significant value for the preparation of mols. bearing a 1,2-diamine motif.

Angewandte Chemie, International Edition published new progress about Diamines Role: SPN (Synthetic Preparation), PREP (Preparation) (chiral). 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