129644-26-4Relevant academic research and scientific papers
Diaryl Ether Formation Merging Photoredox and Nickel Catalysis
Liu, Le,Nevado, Cristina
, p. 2188 - 2193 (2021/05/04)
Photoredox and Ni catalysis are combined to produce diaryl ethers under mild conditions. A broad range of aryl halides and phenol derivatives are cross-coupled in the presence of a readily available organic photocatalyst and NiBr2(dtbpy). Symmetrical diaryl ethers have also been directly obtained from aryl bromides in the presence of water. Mechanistic investigations support the involvement of Ni(0) species at the outset of the reaction and a Ni(II)/Ni(III)-photocatalyzed single electron transfer process preceding the productive C(sp2)-OAr reductive elimination.
Exploring Tandem Ruthenium-Catalyzed Hydrogen Transfer and SNAr Chemistry
Polidano, Kurt,Reed-Berendt, Benjamin G.,Basset, Ana?s,Watson, Andrew J. A.,Williams, Jonathan M. J.,Morrill, Louis C.
, p. 6716 - 6719 (2017/12/26)
A hydrogen-transfer strategy for the catalytic functionalization of benzylic alcohols via electronic arene activation, accessing a diverse range of bespoke diaryl ethers and aryl amines in excellent isolated yields (38 examples, 70% average yield), is reported. Taking advantage of the hydrogen-transfer approach, the oxidation level of the functionalized products can be selected by judicious choice of simple and inexpensive additives.
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.
Efficient palladium-catalyzed coupling reactions of aryl bromides and chlorides with phenols
Hu, Tongjie,Schulz, Thomas,Torborg, Christian,Chen, Xiaorong,Wang, Jun,Beller, Matthias,Huang, Jun
supporting information; scheme or table, p. 7330 - 7332 (2010/06/14)
A convenient and general palladium-catalyzed coupling reaction of aryl bromides and chlorides with phenols was developed. Various functional groups such as nitriles, aldehydes, ketones and esters are well tolerated and the corresponding products are obtained in good to excellent yield.
Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers
Aranyos, Attila,Old, David W.,Kiyomori, Ayumu,Wolfe, John P.,Sadighi, Joseph P.,Buchwald, Stephen L.
, p. 4369 - 4378 (2007/10/03)
A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electronically neutral and electron-rich aryl bromides, chlorides, and triflates can be combined with a variety of phenols with the use of sodium hydride or potassium phosphate as base in toluene at 100 °C. The bulky yet basic nature of the phosphine ligand is thought to be responsible for increasing the rate of reductive elimination of the diaryl ether from palladium.
