22040-02-4

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 83566-43-2 tetraphenyl-bismuth trifluoroacetate 
• 79169-56-5 tetraphenylbismuthonium trifluoroacetate 
• 591-50-4 iodobenzene 
• 608-28-6 2,6-dimethyliodobenzene 
• 123084-61-7 (2,6-dimethylphenyl)-λ³-iodanediyl diacetate 
• 603-33-8 triphenylbismuthane 
• 108-86-1 bromobenzene 
• 16081-16-6 sodium 2,6-dimethylphenolate 
• 108-95-2 phenol 
• 576-22-7 2-Bromo-m-xylene 

Downstream Products

• 576-26-1 2.6-dimethylphenol 

Relevant academic research and scientific papers

Spontaneous generation of chirality in simple diaryl ethers

We studied the spontaneous formation of chiral crystals of four diaryl ethers, 3-phenoxybenzaldehyde, 1; 1,3-dimethyl-2-phenoxybenzene, 2; di(4-aminophenyl) ether, 3; and di(p-tolyl) ether, 4. Compounds 1, 3, and 4 form conformationally chiral molecules i

Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates

High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.

Magnetically recyclable nano copper/chitosan in O-arylation of phenols with aryl halides

Interaction of chitosan (CS) with Fe3O4, followed by embedding Cu nanoparticles (NPs) on the magnetic surface through adsorption of Cu2+, and its reduction to Cuo via NaBH4, offers a reusable efficient catalyst (Fe3O4/CS-Cu NPs) that is employed in cross-coupling reactions of aryl halides with phenols, which affords the corresponding diaryl ethers, with good to excellent yields. The catalyst is completely recoverable from the reaction mixture by using an external magnet. It can be reused four times, without significant loss in its catalytic activity.

Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C-N and C-O coupling reactions

This paper describes an efficient procedure for palladium(0)-catalyzed N-arylation and O-arylation of aryl halides by Ullmann-type cross coupling reaction under mild reaction conditions in a short reaction time. Two phosphine sulphide ligands and their corresponding Pd(0) complexes namely [Pd(p2S2)(dba)] and [Pd(pp3S4)(dba)], were synthesized, where p2S2 is 1,2-bis(diphenylphosphino)ethane disulfide, pp3S4 is tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide and dba is dibenzylideneacetone. Optimal reaction conditions were determined for the arylation reactions using iodobenzene and benzimidazole by varying temperature, solvent, base and catalyst loading. The cross coupling reactions were carried out taking iodobenzenes/bromobenzenes and a wide variety of substituted aryl amines/phenols/alcohols with different steric and electronic properties to afford the desired N-aryl amines/diaryl ethers/alkyl aryl ethers in good to excellent yield (70-94%).

Synthesis of highly functionalized diaryl ethers by copper-mediated O-arylation of phenols using trivalent arylbismuth reagents

Highly functionalized diaryl ethers were prepared by copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes. The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. Highly functionalized diaryl ethers were prepared by a copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes (see scheme). The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. FG=functional group.

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.

Copper-catalyzed Ullmann-type synthesis of diaryl ethers assisted by salicylaldimine ligands

A series of salicylaldimine ligands were designed to promote the copper-catalyzed Ullmann cross-coupling reaction. After a screening process, 2-((2-isopropylphenylimino)methyl)phenol was found to serve as a good supporting ligand for this reaction. Employing this Schiff-base ligand as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. Various diaryl ethers were obtained with excellent yields in dioxane in the presence of K3PO4 and a catalytic amount of copper(I) salt.

Copper(II) trans-bis-(glycinato): An efficient heterogeneous catalyst for cross coupling of phenols with aryl halides

Copper(II) trans-bis-(glycinato) complex, easily prepared by the solid state reaction of copper(II) acetate and glycine (trans-[Cu(glyo) 2·H2O]) was found to be an efficient, recyclable, and high yielding catalyst for the Ullmann type synthesis of diaryl ethers via the cross coupling of phenols with aryl halides without using any additives at relatively low reaction temperature. The catalyst could easily be recovered by simple filtration and was reused for several runs with consistent catalytic activity.

Methenamine as an efficient ligand for copper-catalyzed coupling of phenols with aryl halides

Employing methenamine as a new supporting ligand, the copper-catalyzed coupling reactions of aryl bromides or aryl iodides with various phenols successfully proceeded in good yields under mild conditions. A series of diaryl ethers were obtained with excellent yields in the presence of K 3PO4 and copper(I) salt. Copyright