24789-53-5

Upstream product

• 3058-39-7 4-iodobenzonitrile 
• 108-68-9 3,5-Dimethylphenol 
• 623-00-7 4-bromobenzenecarbonitrile 
• 623-03-0 4-Cyanochlorobenzene 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 100-00-5 4-chlorobenzonitrile 
• 1194-02-1 4-fluorobenzonitrile 

Downstream Products

• 767-00-0 4-cyanophenol 
• 108-68-9 3,5-Dimethylphenol 
• 925005-06-7 4-(3,5-dimethylphenoxy)benzoic acid 
• 1436378-65-2 4-(3,5-dimethylphenoxy)-N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]benzamide 
• 938375-17-8 4-(3,5-dimethylphenoxy)benzylamine 

Relevant academic research and scientific papers

Selective one-pot access to symmetrical or unsymmetrical diaryl ethers by copper-catalyzed double arylation of a simple oxygen source

Great CO-mbination: A novel method is reported for the controlled one-pot synthesis of various symmetrical or unsymmetrical diaryl ethers by double arylation of a simple inorganic oxygen source (see scheme). This versatile and highly selective process is based on the use of a cheap and low toxicity copper catalytic system.

Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis

The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.

CATALYTIC SYSTEM FOR CROSS-COUPLING REACTIONS

The present invention concerns a process for creating a Carbon-Carbon bond (C—C) or a Carbon-Heteroatom bond (C—HE) by reacting a compound carrying a leaving group with a nucleophilic compound carrying a carbon atom or a heteroatom (HE) that can substitute for the leaving group, creating a C—C or C—HE bond, wherein the reaction takes place in the presence of an effective quantity of a. a catalytic system comprising a ligand and at least a metal-based catalyst, such a metal catalyst being chosen among iron or copper compounds proviso that only a single metal is present.

CuI-USY as a Ligand-Free and Recyclable Catalytic System for the Ullmann-Type Diaryl Ether Synthesis

The catalytic potential of copper(I)-exchanged zeolites was evaluated in the Ullmann-type synthesis of diaryl ethers. Among four investigated zeolites (i.e., USY, MOR, β, and ZSM5), CuI-USY was the best catalyst and proved efficient under ligand-free conditions in toluene at 120 °C. CuI-USY was also easy to recover and was recyclable up to five times without significant loss of activity.

On the frontier between nucleophilic aromatic substitution and catalysis

A study on the arylation of heteroatom nucleophiles by using activated haloarenes, with or without metal catalysts, is reported. A discussion concerning the involvement of traces of metals is presented, supported by an unexpected ''ligand'' effect in the absence of added metal catalysts. We believe that the frontier between nucleophilic aromatic substitution and catalysis will likely prove to be much harder to delimit than is generally thought. S NAr or catalysis? A study on the arylation of heteroatom nucleophiles by using activated haloarenes, with or without added metal catalysts, is reported. A discussion concerning the involvement of traces of metals is presented, supported by an unexpected "ligand" effect in the absence of added metal catalysts (see scheme, EWG=electron-withdrawing group).

Discovery of N-{4-[(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl-2- methylpropyl}-4-phenoxybenzamide analogues as selective kappa opioid receptor antagonists

There is continuing interest in the discovery and development of new κ opioid receptor antagonists. We recently reported that N-substituted 3-methyl-4-(3-hydroxyphenyl)piperazines were a new class of opioid receptor antagonists. In this study, we report the syntheses of two piperazine JDTic-like analogues. Evaluation of the two compounds in an in vitro [35S] GTPγS binding assay showed that neither compound showed the high potency and κ opioid receptor selectivity of JDTic. A library of compounds using the core scaffold 21 was synthesized and tested for their ability to inhibit [35S]GTPγS binding stimulated by the selective κ opioid agonist U69,593. These studies led to N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3- methylpiperazin-1-yl]methyl}-2-methylpropyl]-4-phenoxybenzamide (11a), a compound that showed good κ opioid receptor antagonist properties. An SAR study based on 11a provided 28 novel analogues. Evaluation of these 28 compounds in the [35S]GTPγS binding assay showed that several of the analogues were potent and selective κ opioid receptor antagonists.

New Catalytic System for Cross-Coupling Reactions

The present invention concerns a process for creating a Carbon-Carbon bond (C—C) or a Carbon-Heteroatom bond (C-HE) by reacting a compound carrying a leaving group with a nucleophilic compound carrying a carbon atom or a heteroatom (HE) that can substitute for the leaving group, creating a C—C or C-HE bond, wherein the reaction takes place in the presence of an effective quantity of a. a catalytic system comprising a ligand and at least a metal-based catalyst, such a metal catalyst being chosen among iron or copper compounds proviso that only a single metal is present.

COMPOSITION FOR AGRICULTURAL USE FOR CONTROLLING OR PREVENTING PLANT DISEASES CAUSED BY PLANT PATHOGENS

Disclosed is a composition for agricultural use, which is used for controlling or preventing plant diseases caused by plant pathogens. The composition for agricultural use contains a compound represented by formula (1), a salt thereof or a hydrate of the compound or the salt. (1) [In the formula, Z represents an oxygen atom, a sulfur atom or NRz; and E represents a furyl group, a thienyl group, a pyrrolyl group, a tetrazolyl group, a thiazolyl group, a pyrazolyl group, a phenyl group or the like.]

Sol-gel immobilized and reusable copper-catalyst for arylation of phenols from aryl bromides

A simple β-diamide ligand was immobilized by the sol-gel process on hybrid silica for Cu-mediated O-arylation reactions. Combined with 5% of CuI, the latter can easily be recovered and reused to generate diarylethers under smooth conditions from cheap aryl bromides in an eco-friendly solvent (MIBK). Besides, negligible metal leaching occurred after reaction in solution from the supported catalyst.

Copper- or iron-catalyzed arylation of phenols from respectively aryl chlorides and aryl iodides

The utility of diketone-1 was checked, which was first introduced for bimetallic Fe-Cu catalysts, in copper-catalyzed arylation of phenols from aryl chlorides. A systematic study was first undertaken by choosing 3,5-dimethylphenol as a model substrate. The first blank test was undertaken with PhCl and the dieketone-1/[Cu(acac)2] system. The second blank test was performed without copper and showed as expected that the arylation from PhCl did not proceed at all with a catalytic system only based on iron. A protocol permitting the arylation of 3,5-dimethylphenol with chlorobenzene in excellent yield. The system diketone-1//[Cu(acac)2] efficiently promotes cross-coupling reactions between phenols and chlorobenzene or aryl chlorides, which are deactivated by electron-donating substituents. The results indicate that an efficient global method for arylation of phenols from aromatic chlorides can be discovered.