21648-16-8Relevant articles and documents
Method for synthesizing diarylamine through N-arylation reaction of arylamine under copper catalysis
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Paragraph 0062-0063; 0070; 0071; 0080; 0081, (2021/07/14)
The invention provides a method for synthesizing diarylamine through an N-arylation reaction of arylamine under copper catalysis. The method comprises the following steps: S1, selecting a proper amount of a reaction reagent, a catalyst, a solvent and the like; S2, sequentially adding a reaction reagent, a catalyst, a solvent and the like into a reaction tube with a magnetic bar; S3, selecting a proper amount of AcOH, and adding the AcOH into the reaction tube; S4, heating the reaction tube; S5, performing oil bath treatment; S6, cooling to room temperature, and diluting; S7, extracting by using ethyl acetate; S8, washing the organic layer with saline water; S9, drying on anhydrous Na2SO4; S10, evaporating under vacuum; and S11, purifying the residues into the pure product through silica gel chromatography. A scheme that arylamine and an environmentally-friendly and stable aryl silicon reagent are subjected to an N-arylation reaction under the catalysis of a cheap copper reagent is provided, Cu(OAc)2 is used as a catalyst to react in DMSO in the atmosphere of O2, the conversion reactivity is good, the substrate range is wide, and the method has good tolerance to reaction substrates with various functional groups under mild reaction conditions.
Copper complexes of 1,4-diazabutadiene ligands: Tuning of metal oxidation state and, application in catalytic C-C and C-N bond formation
Mukherjee, Aparajita,Basu, Semanti,Bhattacharya, Samaresh
, (2019/11/11)
Reaction of 1,4-diazabutadiene (p-RC6H4N = C(H)(H)C = NC6H4R-p; R = OCH3, CH3, H and Cl; abbreviated as L-R) with CuCl2·2H2O in methanol at ambient temperature (25 °C) affords a group of doubly chloro-bridged dicopper complexes of type [{CuI(L-R)Cl}2], designated as 1-R. Similar reaction carried out in acetonitrile furnishes a family of doubly chloro-bridged dicopper complexes of type [{CuII(L-R)Cl2}2], designated as 2-R. Molecular structures of 1-OCH3 and 2-OCH3 have been determined by X-ray crystallography. While copper(I) is having a nearly tetrahedral N2Cl2 coordination sphere in 1-OCH3, the N2Cl3 coordination sphere around copper(II) is distorted square pyramidal in nature in 2-OCH3. Isolated 2-R complexes, on dissolution in methanol, are found to undergo facile reduction of the metal center to generate the corresponding 1-R complexes. The 1-R and 2-R complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the 1-R and 2-R complexes shows both metal-centered and ligand centered redox responses. The 1-R complexes are found to efficiently catalyze C-N cross-coupling reactions between arylboronic acids and aryl amines; while the 2-R complexes display notable catalytic efficiency for nitroaldol reactions.
Copper-Catalyzed NaBAr 4-Based N-Arylation of Amines
Yang, Qin,Lei, Xiaoli,Yin, Zhijian,Deng, Zhihong,Peng, Yiyuan
supporting information, p. 538 - 544 (2019/01/10)
Using NaBAr 4 as an arylating agent, the formation of carbon-heteroatom bonds by a Cham-Lam cross-coupling reaction in the presence of catalytic copper(II) acetate monohydrate in acetonitrile at room temperature under air is described. The investigation of reaction scope suggests that several aliphatic and aromatic amines are compatible. In particular, the reaction of alkylamine and NaBAr 4 proceeds smoothly to offer the corresponding products in good to excellent yields.
