86718-07-2Relevant articles and documents
N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst
Dindarloo Inaloo, Iman,Majnooni, Sahar,Eslahi, Hassan,Esmaeilpour, Mohsen
, p. 13266 - 13278 (2020/10/07)
An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is
N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent
Wang, Yongbin,Zhang, Yu,Yang, Beibei,Zhang, Ao,Yao, Qizheng
, p. 4101 - 4114 (2015/03/30)
N-(1-Oxy-pyridin-2-ylmethyl)oxalamic acids (L3-L5) were identified as novel efficient ligands for copper-catalyzed C-N cross-coupling of azoles and aryl halides in water. The N-arylation of imidazoles, indoles and pyrazoles proceeded with moderate to excellent yields and complete selectivity over aromatic amines and phenols. Moreover, L5, which is also efficient in organic solvent with low catalyst loading, can be used to promote the N-arylation reactions with water-sensitive materials. The catalytic mechanism was proposed based on the results of several verification experiments which indicated that the ligands as new-type chelators may coordinate to Cu(i) with two oxygen atoms of N-oxide and amide in the coupling process. This journal is
An in situ generated CuI/metformin complex as a novel and efficient catalyst for C-N and C-O cross-coupling reactions
Ghorbani-Vaghei, Ramin,Hemmati, Saba,Veisi, Hojat
, p. 7095 - 7099 (2013/12/04)
An in situ generated complex of copper(I) and a biguanide, namely metformin, was found to be a highly efficient homogeneous catalyst in N/O-arylation reactions. The O-arylation of substituted phenols with various aryl iodides and bromides was also achieved using this copper catalyst to afford diaryl ethers in good to excellent yields in DMF. This heterogeneous copper catalyst also promotes the N-arylation of imidazole with a variety of aryl halides (Cl, Br, I) in acetonitrile.
Highly efficient ci￡n bond forming reactions in water catalyzed by copper(i) iodide with calix[4]arene supported amino acid ionic liquid
Huang, Li,Jin, Can,Su, Weike
, p. 2394 - 2400 (2013/01/15)
A novel and effective protocol has been developed for the Ullmann-type Ci￡N coupling reaction catalyzed by calix[4]arene supported amino acid ionic liquid and copper(I) iodide in water under microwave irradiation condition. The protocol uses calix[4]arene supported amino acid ionic liquid as double function of the ligand and phase-transfer catalyst, and shows good tolerance in good to excellent yields. A novel and effective protocol has been developed for the Ullmann-type Ci￡N coupling reaction catalyzed by calix[4]arene supported amino acid ionic liquid and copper(I) iodide in water under microwave irradiation condition. The protocol uses calix[4]arene supported amino acid ionic liquid as double function of the ligand and phase-transfer catalyst, and shows good tolerance in good to excellent yields. Copyright
Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water
Inamoto, Kiyofumi,Nozawa, Kanako,Kadokawa, Jun,Kondo, Yoshinori
experimental part, p. 7794 - 7798 (2012/09/22)
Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-fr
Electronic effects of para-substitution on the melting points of TAAILs
Schulz, Tobias,Ahrens, Sebastian,Meyer, Dirk,Allolio, Christoph,Peritz, Anke,Strassner, Thomas
supporting information; experimental part, p. 863 - 867 (2011/10/05)
Owing to numerous new applications, the interest in "task- specific" ionic liquids increased significantly over the last decade. But, unfortunately, the imidazolium-based ionic liquids (by far the most frequently used cations) have serious limitations whe
PH-Responsive chelating N-heterocyclic dicarbene palladium(ii) complexes: Recoverable precatalysts for Suzuki-Miyaura reaction in pure water
Li, Liuyi,Wang, Jinyun,Zhou, Chunshan,Wang, Ruihu,Hong, Maochun
body text, p. 2071 - 2077 (2011/09/16)
A hydrophobic palladium complex of the chelating N-heterocyclic dicarbene (NHDC) (3) was synthesized through in situ deprotonation of a bisimidazolium salt (2) by Pd(OAc)2 in DMSO, subsequent basic hydrolysis and acidification resulted in the formation of four NHDC palladium complexes bearing carboxylic functional groups (4-7). Complexes 4-7 are air-stable, pH-responsive and water-soluble under basic conditions due to deprotonation of the carboxylic groups. The catalytic activities of the hydrophilic catalytic systems from 4-7 were preliminarily evaluated using the Suzuki-Miyaura cross-coupling reaction in pure water, high catalytic activity and chemical selectivity were observed in comparison with their hydrophobic analogue from 3. Either the catalytic aqueous solution or the pH-responsive catalysts were easily separated and could be recycled at least four times. TEM analysis revealed that Pd(0) nanoparticles were formed after the catalytic reaction.
Salts Comprising Aryl-Alkyl-Substituted Imidazolium and Triazolium Cations and the Use Thereof
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Page/Page column 8-9; 11, (2011/05/08)
The present invention relates to salts comprising novel aryl-alkyl-substituted imidazolium and triazolium cations and arbitrary anions. The invention further relates to methods for the chemical conversion and separation of substances, comprising the salts
Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride
Phillips, Dean P.,Zhu, Xue-Feng,Lau, Thomas L.,He, Xiaohui,Yang, Kunyong,Liu, Hong
supporting information; experimental part, p. 7293 - 7296 (2010/03/03)
The copper-catalyzed C-N coupling of amides to aryl halides usually requires the use of strong alkali metal bases, such as K2CO3, K3PO4, and Cs2CO3, at high temperature. We discovered that
Highly functional group tolerance in copper-catalyzed N-arylation of nitrogen-containing heterocycles under mild conditions
Zhu, Liangbo,Li, Gaocan,Luo, Liang,Guo, Peng,Lan, Jingbo,You, Jingsong
supporting information; experimental part, p. 2200 - 2202 (2009/07/01)
A copper-catalyzed process has been developed for the N-arylation reaction under very mild conditions in the absence of additional ligand. This protocol could not only tolerate an array of thermally sensitive functional groups, but also achieve high chemoselectivity.
