120957-65-5

Upstream product

• 22445-41-6 3,5-dimethylphenyl iodide 
• 150-76-5 4-methoxy-phenol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 108-68-9 3,5-Dimethylphenol 
• 623-12-1 4-chloromethoxybenzene 
• 556-97-8 1-chloro-3,5-dimethylbenzene 
• 100-17-4 para-methoxynitrobenzene 
• 696-62-8 para-iodoanisole 

Downstream Products

• 100886-05-3 (4-Hydroxy-phenyl)-(3.5-dimethyl-phenyl)-aether 

Relevant academic research and scientific papers

Remarkable stability of copper(II)-N-heterocyclic carbene complexes void of an anionic tether

A library of pyridyl- and picolyl-substituted imidazolium salts have been synthesized and coordinated to copper, via transmetalation from silver(I)-N-heterocyclic carbenes (NHCs), to prepare several copper(I)- and copper(II)-NHC complexes. The copper(I)-NHCs are complexes of the type Cu(NHC)Br, with the solid-state structures revealing a variety of coordination environments around the copper centers. The stability of the copper(II) complexes is particularly unusual, given the absence of a hard anionic tethering group appended to the ligands. The stability has been attributed to the pyridyl substituent, with the complexes being extremely stable, while those with an appended anionic group tend to be more sensitive to air/moisture. The ligands and complexes have been examined in an Ullmann-type etherification reaction and exhibit improved activity in comparison to copper in the absence of a ligand or the common Cu(I)-NHC complexes Cu(IMes)Cl and [Cu(IMes)2]PF6, indicating stabilization of higher oxidation state species by the ligands during the catalytic cycle.

Nitrogen ligands in copper-catalyzed arylation of phenols: Structure/activity relationships and applications

In spite of the importance of ligand/ copper-catalyzed arylations of nucleophiles in organic chemistry, the structural and electronic features that make a ligand efficient in these reactions have not been determined until now. In this work, several bident

Phosphazene P4-But base for the Ullmann biaryl ether synthesis

In the presence of phosphazene P4-But base and CuBr, aryl halides couple with phenols to give biaryl ethers at ca. 100 °C.

Pd-Catalyzed Etherification of Nitroarenes

The Pd-catalyzed etherification of nitroarenes with arenols has been achieved using a new rationally designed ligand. Mechanistic insights were used to design the ligand so that both the oxidative addition and reductive elimination steps of a plausible catalytic cycle were facilitated. The catalytic system established here provides direct access to a range of unsymmetrical diaryl ethers from nitroarenes.

Aromatic ether compound or the sulfhydryl compound

[Problem] Aromatic ether compounds and aromatic sulfide compound of this new technology to[Solution] In general formula (1a), (1b), (1c) palladium or nickel compound or a phosphine compound represented by the compound comprising a transition metal compound in the presence of a transition metal catalyst, (A1) is represented by compounds having hydroxy carbon C a-OH or (A2) with a compound represented by the sulfhydryl carbon C a-SH, nitro group (- NO2 ) To react with an aromatic nitro compound (B), (A1) to the compound of the aromatic nitro compound (C1) or the reaction product of an aromatic ether compounds (B) hetero coupling (A2) of the compounds of the reaction product of an aromatic sulfide compound of an aromatic nitro compound (C2) generating (B) hetero coupling characterized by comprising the step of, aromatic ether compounds or aromatic sulfide compound. [Drawing] no

Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides

The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.

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.

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.

A green approach for arylation of phenols using iron catalysis in water under aerobic conditions

The first efficient iron-catalyzed coupling of aryl iodides with phenols was developed exclusively with water as solvent. The reaction is performed with low cost and readily available FeCl3·6H2O and DMEDA catalytic system providing diaryl ethers in good to excellent yields. The effectiveness of this reaction was further revealed by compatibility with a wide range of functional groups. Moreover, the procedure is rendered simple as this transformation is carried out in the presence of air. Thus, the protocol represents a facile, economical and eco-friendly procedure to access diaryl ethers.

Green alternative solvents for the copper-catalysed arylation of phenols and amides

Investigation of the use of green organic solvents for the Cu-catalysed arylation of phenols and amides is reported. Alkyl acetates proved to be efficient solvents in the catalytic processes, and therefore excellent alternatives to the typical non-green solvents used for Cu-catalysed arylation reactions. Solvents such as isosorbide dimethyl ether (DMI) and diethyl carbonate also appear to be viable possibilities for the arylation of phenols. Finally, a novel copper catalysed acyl transfer process is reported.