875838-68-9Relevant academic research and scientific papers
Magnetically recyclable nano copper/chitosan in O-arylation of phenols with aryl halides
Mousavi Mashhadi, Seyed Ali,Kassaee, Mohamad Z.,Eidi, Esmaiel
, (2019/07/04)
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.
Green alternative solvents for the copper-catalysed arylation of phenols and amides
Sambiagio, Carlo,Munday, Rachel H.,John Blacker,Marsden, Stephen P.,McGowan, Patrick C.
, p. 70025 - 70032 (2016/08/06)
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.
Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and Heteroarenes
Sokolovs, Igors,Suna, Edgars
, p. 371 - 379 (2016/01/25)
Cu-catalyzed reaction of phenols with electron-rich arene or heteroarene ligands of unsymmetrical diaryl-λ3-iodanes is a key step in the developed one-pot two-step method for intermolecular para-selective C-H aryloxylation of heteroarenes and arenes.
Picolinamides as effective ligands for copper-catalysed aryl ether formation: Structure-activity relationships, substrate scope and mechanistic investigations
Sambiagio, Carlo,Munday, Rachel H.,Marsden, Stephen P.,Blacker, A. John,McGowan, Patrick C.
supporting information, p. 17606 - 17615 (2015/02/05)
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.
