223762-69-4Relevant academic research and scientific papers
A waste-minimized protocol for copper-catalyzed Ullmann-type reaction in a biomass derived furfuryl alcohol/water azeotrope
Ferlin, Francesco,Trombettoni, Valeria,Luciani, Lorenzo,Fusi, Soliver,Piermatti, Oriana,Santoro, Stefano,Vaccaro, Luigi
supporting information, p. 1634 - 1639 (2018/04/12)
We report the use of biomass-derived furfuryl alcohol as an effective bidentate ligand able to promote the Ullmann-type copper-catalyzed coupling of aryl halides with heteroaromatic or aliphatic amines. Furfuryl alcohol (FA) can be mixed with water to form the corresponding azeotrope (20 wt% of FA) and therefore can be easily recovered and reused. This protocol is efficiently applied to substrates with various electronic nature and affords the expected products (27 examples) in generally good to excellent yields. It has also been demonstrated that the protocol is both chemically and environmentally effective as the azeotropic mixture can be easily and almost quantitatively recovered at the end of the process.
Cu2O/Cs2CO3/DMF: An efficient catalytic system for N-arylation of imidazole with aryl halides under ligand-free conditions
Wang, Xiaochuang,Wang, Meiji,Xie, Jianwei
supporting information, p. 1797 - 1803 (2017/09/22)
A ligand-free Cu-catalyzed protocol for the Ullmann-type N-arylation of N-containing heterocycles with aryl or heteroaryl iodides and bromides has been established. A broad range of functional groups is well tolerated on both of the cross-coupling partners, producing the desired products in good to excellent yields.
Copper-catalysed N-arylation of pyrrole with aryl iodides under ligand-free conditions
Liu, Lili,Wu, Fengtian,Liu, Yan,Xie, Jianwei,Dai, Bin,Zhou, Zhuoqiang
, p. 180 - 182 (2014/04/17)
A simple, inexpensive and ligand-free copper-catalysed N-arylation of pyrrole with aryl iodides has been developed giving N-arylated products in moderate to excellent yields. The catalyst loading is relative low (5 mol%) and the catalyst system was stable in air.
An unusual 30-membered copper(i) cluster derived from the C-S bond cleavage and its use in heterogeneous catalysis
Li, Hong-Xi,Zhao, Wei,Li, Hai-Yan,Xu, Zhong-Lin,Wang, Wen-Xia,Lang, Jian-Ping
supporting information, p. 4259 - 4261 (2013/07/05)
The Cu(i)-mediated C-S bond cleavage of 5-methyl-4-(p-tolyl)pyrimidine-2- thiol (mtpmtH) gave one 30-nuclear cluster [Cu30I16(mtpmt) 12(μ10-S4)], one polymeric complex [(bmtpms)Cu-(μ-I)]n and one tetranuclear complex [(bmptmds){Cu(μ-I)}2]2; the 30-nuclear cluster displayed excellent catalytic performances in the coupling reactions of N-heterocycles and arylboronic acids and could be recycled and reused.
Tetrazole-1-acetic acid as a ligand for copper-catalyzed N-arylation of imidazoles with aryl iodides under mild conditions
Wu, Feng-Tian,Liu, Ping,Ma, Xiao-Wei,Xie, Jian-Wei,Dai, Bin
, p. 893 - 896 (2013/09/24)
Tetrazole-1-acetic acid was found to serve as a superior ligand for CuI-catalyzed N-arylation of imidazoles with aryl iodides under a low catalyst loading (5 mol% of CuI). A variety of aryl iodides could be aminated to provide the N-arylated products in good to excellent yields without the need of an inert atmosphere.
Efficient copper-catalyzed ullmann reaction of aryl bromides with imidazoles in water promoted by a pH-Responsive ligand
Lv, Rui,Wang, Yangxin,Zhou, Chunshan,Li, Liuyi,Wang, Ruihu
, p. 2978 - 2982 (2013/10/21)
A series of 1,10-phenanthroline derivatives were used as supporting ligands for copper-catalyzed Ullmann reaction in neat water. The catalytic system based on 4,7-dihydroxy-1,10-phenanthroline has demonstrated the promising catalytic performances for aryl
Nitrogen-rich copolymeric microsheets supporting copper nanoparticles for catalyzing arylation of N-heterocycles
Huang, Zhijun,Li, Fengbo,Chen, Bingfeng,Xue, Fei,Chen, Guochang,Yuan, Guoqing
experimental part, p. 104 - 111 (2012/01/03)
Nitrogen-rich copolymeric microsheets were synthesized through incomplete condensation of melamine and cyanuric chloride. The materials can be well-dispersed in polar solvent and perform excellently as supports or stabilizing agents for metal nanoparticles. The presence of nitrogen in the lattice improves their interaction with the copper nanoparticle precursor (Cu(II) ions). Monodispersed copper nanoparticles over these supports were obtained after reducing the absorbed precursors. The materials were characterized by powder X-ray diffraction (XRD), transmission electron microscopy (TEM), and X-ray photoelectron spectroscopy (XPS). The catalytic C-N coupling reaction was selected as the model reaction to evaluate the catalytic performance of the supported nanoparticles. The catalysts show above 90% yield of coupling products and retain activity after a five-run recycling test. Surface chemistry and morphology transforming during the catalytic process was further investigated. Nitrogen-rich copolymeric microsheets were proven to be excellent supports and stabilizing agents for metal nanoparticles.
Unexpected reactivity resulting from modifications of the ligand periphery: Synthesis, structure, and spectroscopic properties of iron complexes of new tripodal N-heterocyclic carbene (NHC) ligands
Vogel, Carola S.,Heinemann, Frank W.,Khusniyarov, Marat M.,Meyer, Karsten
scheme or table, p. 226 - 237 (2011/02/28)
The chelating ligand tris-[2-(3-aryl-imidazol-2-ylidene)ethyl]amine (TIMENR, R = aryl = 2,6-xylyl (xyl), mesityl (mes)) has provided access to reactive transition metal complexes. Here, two new tripodal N-heterocyclic carbene ligands of the TIM
Efficient copper-catalyzed N-arylations of nitrogen-containing heterocycles and aliphatic amines in water
Li, Xufeng,Yang, Daoshan,Jiang, Yuyang,Fu, Hua
experimental part, p. 1097 - 1105 (2010/08/06)
A simple and efficient copper-catalyzed method has been developed for N-arylations of nitrogen-containing heterocycles and aliphatic amines in water. The protocol uses (1E,2E)-oxalaldehyde dioxime (OADO) as the ligand, and water as the solvent, and shows good tolerance towards various functional groups.
N-arylations of nitrogen-containing heterocycles with aryl and heteroaryl halides using a copper(I) oxide nanoparticle/1,10-phenanthroline catalytic system
Tang, Bo-Xiao,Guo, Sheng-Mei,Zhang, Man-Bo,Li, Jin-Heng
, p. 1707 - 1716 (2008/12/22)
A general procedure for solvent-free N-arylations of nitrogen-containing heterocycles, i.e. imidazoles, triazoles, and indoles, with aryl and heteroaryl halides catalyzed by copper(I) oxide (Cu2O) nanoparticles is demonstrated. Four types of Cu2O were evaluated: the bulky compound and its cubic, octahedral, and spherical nanoparticulate forms. The results show that Cu2O nanoparticles, in particular the cubic form, are highly efficient for the N-arylation reaction. In the presence of cubic Cu2O nanoparticles, 1,10-phenanthroline, and tetrabutylammonium fluoride, a variety of nitrogen-containing heterocycles smoothly underwent N-arylation with aryl and heteroaryl halides at 110-145 °C to give the corresponding products in moderate to excellent yields. It is noteworthy that the reaction is conducted under solvent-free conditions. The reaction mechanism is also discussed.
