25855-75-8

Upstream product

• 63411-81-4 benzoyl-resorcinol 
• 77-78-1 dimethyl sulfate 
• 634-36-6 1,2,3-trimethoxybenzene 
• 98-88-4 benzoyl chloride 
• 127595-53-3 1-(2,6-dimethoxyphenyl)benzyl alcohol 
• 151-10-0 1,3-Dimethoxybenzene 
• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 100-47-0 benzonitrile 
• 93-97-0 benzoic acid anhydride 
• 23112-96-1 (2,6-dimethoxyphenyl)boronic acid 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 66185-72-6 7-(phenylcarbonyl)oxy-4-methyl-2H-1-benzopyran-2-one 

Downstream Products

• 63411-81-4 benzoyl-resorcinol 
• 124937-93-5 N-(3-(2,6-dimethoxyphenyl)-3-hydroxy-3phenylpropylidene)tert.butylamine 
• 1027522-54-8 (2-Benzoyl-3-hydroxy-phenoxy)-acetic acid methyl ester 
• 193738-65-7 4-Hydroxy-3-phenyl-benzofuran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Tetra- And Dinuclear Palladium Complexes Based on a Ligand of 2,8-Di-2-pyridinylanthyridine: Preparation, Characterization, and Catalytic Activity

Complexation of L [L = 5-phenyl-2,8-di-2-pyridinyl-anthyridine] with [Pd(CH3CN)4](BF4)2 and [Pd(CH3CN)3Cl](BF4) in a molar ratio of 1:2 rendered the corresponding dinuclear complexes [Pd2L (CH3CN)4](BF4)4 (1) and [Pd2L (CH3CN)2Cl2](BF4)2 (2), respectively. However, treatment of L with (COD)PdCl2 followed by anion exchange yielded a tetranuclear complex [Pd4L3Cl4](PF6)4(4a). Structures of these complexes are characterized by both spectroscopy and X-ray crystallography. Interconversion of these three complexes was studied via the manipulation of stoichiometric ratio of ligand to metal precursor. The catalytic activity of these complexes for carbonylative Suzuki-Miyaura cross-coupling was investigated. Complex 2 shows an excellent catalytic activity on the reaction of aryl iodide with arylboronic acid in the presence of atmospheric pressure of CO to give the corresponding benzophenones.

Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation

Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.

Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction

The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.

An efficient and green method for regio- and chemo-selective Friedel-Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl2]3)

[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel-Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.

An improved palladium(II)-catalyzed method for the synthesis of aryl ketones from aryl carboxylic acids and organonitriles

A palladium(II)-catalyzed decarboxylative protocol for the synthesis of aryl ketones has been developed. The addition of TFA was shown to improve the reaction yield and employing THF as solvent enabled the use of solid nitriles and in only a small excess. Using this method, five different benzoic acids reacted with a wide range of nitriles to produce 29 diverse (hetero)aryl ketone derivatives in up to 94% yield.

Synthesis of aryl ketones by palladium(II)-catalyzed decarboxylative addition of benzoic acids to nitriles

An efficient, sustainable method for the preparation of aryl ketones from ortho-substituted benzoic acids proceeds through their decarboxylation to generate an aryl-palladium species, followed by addition to a nitrile and hydrolysis of the intermediate ketimine.

Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-Crafts acylation of aromatic compounds under solvent-less conditions

Stable and non-hygroscopic aluminum dodecatungstophosphate (AlPW 12O40), which is prepared easily from cheap and commercially available compounds was found to be an effective catalyst for Friedel-Crafts acylation reactions using carboxylic acids, acetic anhydride and benzoyl chloride in the absence of solvent under mild reaction conditions.

Benzofuran derivatives as ET(A)-selective, non-peptide endothelin antagonists

The synthesis and SAR relationships of a series of 4-benzyloxy-3-methylbenzofuran-2-carboxylic acids are described. Compounds from this series show 2- to 16-fold selective binding to the ET(A) receptor in the micromolar range, and two compounds from this series (32 and 40) were demonstrated to exhibit ET(A) antagonist activity.

Regioselective Reductive Electrophilic Substitution of 1,2,3-Trimethoxybenzene and Its 5-Alkyl-Substituted Homologues

The methoxy group in the 2-position of 1,2,3-trimethoxybenzene (1) can be regioselectively removed by electron transfer from alkali metals and replaced with a variety of electrophiles in a one-pot procedure, affording 2-substituted resorcinol dimethyl ethers.The usefulness of this synthetic method is illustrated by numerous examples.This reaction procedure has been successfully extended to the 5-methyl-substituted homologue (2), but limitations occur with the higher homologue 1-pentyl-3,4,5-trimethoxybenzene (3).Investigations on the mechanism of demethoxylation, with the aid of labeling experiments, provided clear evidence for the intermediacy of aryl radicals and explained the low yields obtained in the reductive electrophilic substitution of compound 3.