3096-81-9Relevant articles and documents
Ligand-free copper-catalyzed coupling of phenols with nitroarenes by using a metal-organic framework as a robust and recoverable catalyst
Phan, Nam T. S.,Nguyen, Tung T.,Nguyen, Vu T.,Nguyen, Khoa D.
, p. 2374 - 2381 (2013)
A highly porous metal-organic framework Cu2(BDC)2(DABCO) (H2BDC=1,4-benzenedicarboxylic acid, DABCO=1,4-diazabicyclo[2.2.2]octane) was synthesized and used as an efficient recyclable heterogeneous catalyst for the coupling reaction of phenols with nitroarenes to form diaryl ethers without using a ligand. Physical characterization of the MOF was obtained by using XRD, SEM, TEM, thermogravimetric analysis (TGA), FTIR spectroscopy, atomic absorption spectrophotometry (AAS), H2 temperature-programmed reduction (H2-TPR), and N2 physisorption measurements. The Cu2(BDC)2(DABCO)-catalyzed coupling reaction offers several advantages compared to the conventional Ullmann reaction for the synthesis of unsymmetrical diaryl ethers. To the best of our knowledge, the ligand-free Cu-catalyzed O-arylation reaction of phenols with nitroarenes that uses a heterogeneous catalyst has not been mentioned previously in the literature.
Palladium-catalyzed formation of diaryl ethers from aryl bromides. Electron poor phosphines enhance reaction yields
Mann, Grace,Hartwig, John F.
, p. 8005 - 8008 (1997)
Aryl bromides were converted to diaryl ethers with sodium aryl oxides in the presence of catalytic amounts of Pd(DBA)2 and DPPF. Isolated yields of over 90% were achieved in reactions with electron deficient aryl bromides and electron rich sodium aryl oxides. Electron poor DPPF derivatives led to increased reaction yields.
Nickel-Catalyzed Cyanation of Aryl Thioethers
Delcaillau, Tristan,Woenckhaus-Alvarez, Adrian,Morandi, Bill
supporting information, p. 7018 - 7022 (2021/09/13)
A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.
Light-emitting diode light–enabled denitrative etherification of 4-nitrobenzonitrile under catalyst-free conditions at room temperature
Soltani, Roghaye,Abdollahi, Fatemeh,Ghaderi, Arash
, p. 56 - 59 (2020/06/09)
In this study, we have developed a catalyst-free procedure for denitrative etherification of electron-deficient nitroarenes. In this method, the reaction failed in the dark but was enabled by white light-emitting diode light (6 W) in the presence of NaOH/dimethylformamide at room temperature with short reaction times. Interestingly, the reaction in the dark is completed almost immediately once a small quantity of water is added to the reaction mixture. Ultraviolet irradiation (λ = 254 nm) was not effective for this reaction to proceed.