102908-37-2Relevant articles and documents
Salen-Cu(II) complex catalysed N-arylation of pyrazole under mild conditions
Liu, Yan,Liu, Wei,Zhang, Qin,Liu, Ping,Xie, Jian-Wei,Dai, Bin
, p. 636 - 637 (2013)
Three inexpensive and air-/moisture-stable complexes (Salden)Cu (Salden = N, N'-bis(salicylidene)-1,2-dimethylethylenediamine), (Saldch)Cu (Saldch = N, N'-bis(salicylidene)-1,2-cyclohexenediamine), and (Salph)Cu (salph = N, N'-bis(salicylidene)-1,2-phenylenediamine) were synthesised and evaluated as catalysts for the N-arylation of pyrazole with aryl halides. A variety of aryl iodides and bromides underwent coupling with pyrazole, promoted by the (Saldch)Cu complex, in moderate to excellent yields without the protection by an inert gas.
Efficient cross-coupling reactions of nitrogen nucleophiles with aryl halides in water
Teo, Yong-Chua
, p. 720 - 724 (2009)
A facile and practical strategy has been developed for the N-arylation of nitrogen nucleophiles with aryl halides catalyzed by a combination of iron(III) chloride [FeCl3] and dimethylethylenediamine (dmeda) in water. A variety of nitrogen nucleophiles including pyrazole, indole, 7-azaindole and benzamide afforded the N-arylated products in the presence of the catalytic system (in up to 88% yield).
A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water
Teo, Yong-Chua,Yong, Fui-Fong,Lim, Gina Shiyun
, p. 7171 - 7174 (2011)
An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to 94%) under the described arylation conditions.
C?N Cross-Coupling Reactions Under Mild Conditions Using Singlet Di-Radical Nickel(II)-Complexes as Catalyst: N-Arylation and Quinazoline Synthesis
Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Das, Siuli,van Leest, Nicolaas Petrus,Paul, Nanda D.
, p. 4342 - 4353 (2019)
Herein we report a cost-effective synthetic approach for C?N cross-coupling reactions of a broad array of nitrogen nucleophiles and aryl halides under mild conditions. These reactions are catalyzed by an inexpensive, air-stable, earth-abundant and easy-to-prepare singlet di-radical nickel(II)-catalyst containing two antiferromagnetically coupled single-electron oxidized diiminosemiquinonato type ligands. This protocol provides an alternative method for C?N cross-coupling reactions avoiding nickel(0)/nickel(II) or nickel(I)/nickel(III) redox processes via cooperative participation of metal and ligand-centered redox events. Besides a wide range of N-arylation reactions, by judicious choice of aryl halides and nitrogen nucleophiles the synthesis of a variety of polysubstituted quinazolines has been achieved in moderate to good yields under relatively mild reaction conditions. Our catalyst has been found to be almost equally effective in quinazoline synthesis via C?N cross-coupling of (i) 2-bromobenzylamine with benzamide, and (ii) 2-bromobenzylbromide with amidine. Control experiments and DFT studies were performed to improve the understanding of the cooperative participation of ligand and metal (nickel)-centered redox events during oxidative addition/reductive elimination processes of the catalytic cycle and to shed light on the plausible mechanistic pathway of the C?N cross-coupling reactions. (Figure presented.).
Ligand-free copper-catalyzed N-arylation of nitrogen nucleophiles
Correa, Arkaitz,Bolm, Carsten
, p. 2673 - 2676 (2007)
Versatile, simple and inexpensive ligand-free, copper-catalyzed N-arylations of sulfoximines and nitrogen-containing heterocycles have been developed affording N-arylated products in high yields.
Dehydrogenative Azolation of Arenes in a Microflow Electrochemical Reactor
Buglioni, Laura,Besla?, Marko,No?l, Timothy
supporting information, p. 16195 - 16203 (2021/09/13)
The electrochemical synthesis of aryl azoles was performed for the first time in a microflow reactor. The reaction relies on the anodic oxidation of the arene partners making these substrates susceptible for C-H functionalization with azoles, thus requiring no homogeneous transition-metal-based catalysts. The synthetic protocol benefits from the implementation of a microflow setup, leading to shorter residence times (10 min), compared to previously reported batch systems. Various azolated compounds (22 examples) are obtained in good to excellent yields.
The Hofmann reaction involving annulation of: O -(pyridin-2-yl)aryl amides selectively and rapidly leads to potential photocatalytically active 6 H -pyrido[1,2- c] quinazolin-6-one derivatives
Gao, Wenjing,Liu, Tongxin,Wan, Yameng,Wu, Hao,Zhang, Guisheng,Zhang, Zhiguo
supporting information, p. 7955 - 7961 (2020/11/30)
A highly efficient PIFA-mediated Hofmann reaction of o-(pyridin-2-yl)aryl amides has been developed to selectively and rapidly construct various potential photocatalytically active 6H-pyrido[1,2-c]quinazolin-6-one derivatives. The use of a nontoxic and ec
