105372-24-5

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 609-08-5 Diethyl methylmalonate 
• 104-21-2 p-methoxybenzyl acetate 
• 130728-22-2 4-methoxybenzyl 2,3,4,5,6-pentafluorobenzoate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 270921-39-6 (4-methoxyphenyl)methyl methyl carbonate 

Downstream Products

• 52427-11-9 3-(4-methoxyphenyl)-2-methylpropionic acid 

Relevant academic research and scientific papers

Room-Temperature Benzylic Alkylation of Benzylic Carbonates: Improvement of Palladium Catalyst and Mechanistic Study

The palladium catalyst for the nucleophilic substitution of benzyl carbonates was improved by using 1,1′-bis(diisopropylphosphino)ferrocene (DiPrPF) as the ligand. The [Pd(η3-C3H5)(cod)]BF4-DiPrPF catalyst allows the benzylic substitution with soft carbanions to proceed even at 30 °C, affording the desired products in high yields (up to 99% yield). Thermally unstable pyridylmethyl esters are employable as the electrophilic substrates for the benzylic alkylation with the improved catalyst. Furthermore, we investigated the mechanism of the catalytic benzylic alkylation by means of DiPrPF ligand. The palladium(0) complex bearing DiPrPF activates the benzylic C-O bond to form the (benzyl)palladium(II) intermediate at room temperature. The coordination mode of the benzyl ligand would be equilibrium between the η1- and η3-manner. The nucleophile would preferentially react with the η3-benzyl ligand to give the desired product.

MODULAR CHEMICAL PROBE FOR DETECTION OF AMINO ACID CITRULLINE IN PHYSIOLOGICAL SAMPLES

An improved chemical probe for the detection of the amino acid citrulline combines: 1) a reactive head formed of 1,3-dicarbonyl moiety that reacts with a citrulline side chain in an improved manner compared to currently used 1,2-dicarbonyl moieties; and 2) a modular action of the probe where citrulline side chains are labeled first using reactive heads described above, and attachment of a read-out subunit or tag, be it a fluorophore, a nanoparticle, or an antigen is performed separately. The modular nature of the chemical probe increases the sensitivity of the probes due to their smaller size. Additionally, the chemical probes of the present disclosure allow the same sample to be analyzed using a variety of read-out methods.

Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile

The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-pentafluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the ??1- A nd ??3-benzylnickel intermediates.

Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters

The palladium complex prepared in situ from [Pd(η3-C3H5)(cod)]BF4 and bidentate phosphine DPPF was a good catalyst for the nucleophilic substitution of benzyl acetate. Significant acceleration of the palladium-catalyzed substitution was observed when an alcohol was employed as a reaction solvent. The palladium catalyst was effective for the benzylation of various stabilized carbanions, amines, and benzenesulfinate with benzylic acetates.

Palladium-catalyzed benzylation of active methine compounds without additional base: Remarkable effect of 1,5-cyclooctadiene

(Chemical Equation Presented) The palladium complex prepared from DPPF and Cp(η3-C3H5)Pd is an effective catalyst for the alkylation of active methine compounds with benzylic carbonates under neutral conditions. The additi

Syntheses of 5-, 7-, and 8-Methoxy-3-methyl-2-tetralone

Two efficient syntheses of 5-methoxy- and 8-methoxy-3-methyl-2-tetralone and the synthesis of the 7-methoxy isomer via a different route are described.Also reported is the synthesis of 8-methoxy-3,3-dimethyl-2-tetralone.The regioselectivity of lithium carbanion formation in 1,6-, 1,7-, and 2,7-dihydroxynaphthalene is discussed.The latter compound undergoes dimetalation more easily than the other isomers.