2444-29-3

Upstream product

• 3235-09-4 potassium o-cresolate 
• 586-78-7 para-nitrophenyl bromide 
• 95-48-7 ortho-cresol 
• 100-00-5 4-chlorobenzonitrile 
• 350-46-9 4-Fluoronitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 100-25-4 para-dinitrobenzene 

Downstream Products

• 2093-27-8 (4-chloro-2-methyl-phenyl)-(4-nitro-phenyl)-ether 
• 56705-83-0 4-(2-methylphenoxy)aniline 
• 6082-87-7 o-carboxyphenyl p-nitrophenyl ether 
• 1018853-62-7 acetic acid-(4-o-tolyloxy-anilide) 
• 38100-82-2 (4-bromo-2-methyl-phenyl)-(4-nitro-phenyl)-ether 
• 47000-27-1 (4-Chlormethyl-2-methyl-phenyl)-(4-nitro-phenyl)-ether 
• 212189-50-9 methyl2-(4-nitrophenoxy)benzoate 
• 212189-58-7 methyl2-(4-aminophenoxy)benzoate 
• 116530-27-9 (3-nitro-phenyl)-o-tolyl ether 
• 873980-52-0 2-nitro-4-o-tolyloxy-aniline 
• 873977-69-6 acetic acid-[4-(4-chloro-2-methyl-phenoxy)-anilide] 
• 873977-86-7 acetic acid-[4-(4-bromo-2-methyl-phenoxy)-anilide] 
• 873980-50-8 4-(4-chloro-2-methyl-phenoxy)-2-nitro-aniline 
• 873386-88-0 4-(4-bromo-2-methyl-phenoxy)-2-nitro-aniline 

Relevant academic research and scientific papers

Novel cobalt-valine catalyzed O-arylation of phenols with electron deficient aryl iodides

Abstract: A Novel cobalt-catalyzed O-arylation of phenols with electron deficient aryl iodides is described. The reaction employs cheap and easy-to-handle cobalt acetate tetrahydrate as the catalyst precursor and naturally occurring l-valine as the ligand without the use of any transmetallating or reducing agents. The new protocol offers a wide scope for a variety of phenols towards O-arylation with moderate to excellent yields with electron deficient aryl iodides.

N-Picolinamides as ligands in Ullman type C–O coupling reactions

Copper-catalyzed modified Ullmann coupling reactions creating C–O bonds, including diaryl ethers or phenols, are vital to organic synthesis. Synthesized N-phenyl-2-pyridinecarboxamide and its derivatives were used as ligands in conjunction with catalytic copper sources in the formation of various diaryl ethers and phenols. Various aryl and heteroaryl halides with electron donating and withdrawing groups were reacted with various phenols under mild reaction conditions providing moderate to excellent yields.

Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding Ki and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both Gq-coupled intracellular Ca2+ flux and Gs-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

Ullmann Coupling Reaction of Nitro-Substituted Aryl Halides with Phenols under Mild Conditions: Micro-/Mesoporous Hierarchical LaAlPO-5 Zeolite Catalyst

Heterogeneous catalytic reactions of aromatic organic molecules over zeolite catalysts present many challenges because of the shape selectivity of the micropores of conventional zeolites that limits the diffusion of aromatic molecules. Herein, Ullmann coupling reactions of phenols with nitro-substituted aryl halides were catalyzed by rare-earth-doped mesoporous AlPO-5 zeolites in the absence of ligands. The AlPO-5-MAlPO-5-M zeolites had a pure AFI structure and consisted of spherical particles assembled by nanofibers. The rare-earth elements were highly dispersed in the AlPO-5-MAlPO-5-M samples. The LaAlPO-5-MAlPO-5-M zeolite is an excellent catalyst for Ullmann coupling reactions of phenols and nitro-substituted aryl halides. Mesoporous LaAlPO-5 has an excellent stability and recyclability in the Ullmann coupling of p-X-nitrobenzene (X=Cl, Br, and I) with 2-naphthol. These results are important in the exploration of attractive Ullmann coupling reactions and in the development of mesoporous zeolite catalysts for other organic reactions.

Picolinamides as effective ligands for copper-catalysed aryl ether formation: Structure-activity relationships, substrate scope and mechanistic investigations

The use of picolinic acid amide derivatives as an effective family of bidentate ligands for copper-catalysed aryl ether synthesis is reported. A fluorine-substituted ligand gave good results in the synthesis of a wide range of aryl ethers. Even bulky phenols, known to be very challenging substrates, were shown to react with aryl iodides with excellent yields using these ligands. At the end of the reaction, the first examples of end-of-life Cu species were isolated and identified as CuII complexes with several of the anionic ligands tested. A preliminary mechanistic investigation is reported that suggests that the substituents on the ligands might have a crucial role in determining the redox properties of the metal centre and, consequently, its efficacy in the coupling process. An understanding of these effects is important for the development of new efficient and tunable ligands for copper-based chemistry.

Palladium nanoparticles supported on silica diphenylphosphinite as efficient catalyst for C-O and C-S arylation of aryl halides

Silica diphenylphosphinite (SDPP) can be easily obtained through direct phosphorylation of silica gel. Further reaction of SDPP with Pd(II) produces nano Pd(0)/SDPP. This nano Pd(0) catalyst exhibits excellent reactivity for the C-O and C-S arylation of different aryl iodides, bromides and chloride with phenols and thiophenols. This heterogeneous catalyst shows excellent recyclability and can be easily recovered and reused for several runs. Copyright

First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols

The first palladium-catalyzed protocol for the denitrated coupling reaction of nitroarenes with phenols has been developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. The cyclopalladated ferrocenylimine (catalyst Ic) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol%) and short reaction time (2 h). The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations. Copyright

PROCESS FOR THE CATALYTIC SYNTHESIS OF DIARYL ETHERS

Described is a process for preparing diaryl ethers of the formula (I) [in-line-formulae]Ar—O—Ar′??(I)[/in-line-formulae]In which Ar is an aryl or substituted aryl group and Ar′ is an aryl, substituted aryl, heteroaryl or substituted heteroaryl group,by reacting an aryl of formula (II) or a aryloxy salt of formula (III) [in-line-formulae]Ar—OH ??(II)[/in-line-formulae] [in-line-formulae]Ar—OR ??(III)[/in-line-formulae]In which Ar has the same meaning as in formula (I) and R is an alkali metal,with an aryl or heteroaryl bromide of formula (IV) [in-line-formulae]Ar′—Br ??(IV)[/in-line-formulae]In which Ar′ has the same meaning as in formula (I),characterized in that the reaction is carried out in the presence of a copper(I)salt and a 1-substituted imidazole as catalyst system.

Copper-catalyzed Ullmann coupling under ligand- and additive- free conditions. Part 1: O-Arylation of phenols with aryl halides

O-Arylation of a wide variety of substituted phenols and aliphatic alcohols with aryl halides catalyzed by copper iodide under mild ligand and additive free conditions (nBu4NBr, DMF, K3PO4, reflux, 22 h) is accomplished in good to excellent product yields (up to 95%).

Bio-inspired copper catalysts for the formation of diaryl ethers

Aryl bromides and phenols are coupled efficiently to the corresponding diaryl ethers in the presence of a practical Cu(I)/1-butylimidazole catalyst system. The convenient protocol is applied successfully to the synthesis of 16 different diaryl ethers in high yield and selectivity.