102908-37-2Relevant academic research and scientific papers
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.
Iron-Catalyzed/Mediated C-N Bond Formation: Competition between Substrate Amination and Ligand Amination
Sinha, Suman,Sikari, Rina,Sinha, Vivek,Jash, Upasona,Das, Siuli,Brand?o, Paula,Demeshko, Serhiy,Meyer, Franc,De Bruin, Bas,Paul, Nanda D.
, p. 1935 - 1948 (2019)
Iron catalyzed carbon-nitrogen bond formation reactions of a wide variety of nucleophiles and aryl halides using well-defined iron-complexes featuring redox noninnocent 2-(arylazo)-1,10-phenanthroline (L1) ligands are reported. Besides substrate centered C-N coupling, C-N bond formation reactions were also observed at the ortho- and para-positions of the phenyl ring of the coordinated azo-aromatic scaffolds affording new tetradentate ligands, 2-N-aryl-(2-arylazo)-1,10-phenanthroline (L2), and tridentate ligands, 4-N-aryl-(2-arylazo)-1,10-phenanthroline (L3), respectively. Control experiments and mechanistic studies reveal that the complex [FeL1Cl2] (1) undergoes in situ reduction during the catalytic reaction to produce the monoanionic complex [1]-, which then acts as the active catalyst. The metal (iron) and the coordinated ligand were found to work in a cooperative manner during the transfer processes involved in the fundamental steps of the catalytic cycle. Detailed experimental and theoretical (DFT) studies were performed to get insight into the competitive substrate versus ligand centered amination reactions.
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).
Ruthenium-Catalyzed ortho- And meta-H/D Exchange of Arenes
Zhao, Liang-Liang,Liu, Wei,Zhang, Zengyu,Zhao, Hongyan,Wang, Qi,Yan, Xiaoyu
, p. 10023 - 10027 (2019)
Ruthenium-catalyzed aromatic H/D exchange in [D4]acetic acid has been developed. By using N-heteroarenes as directing groups, both ortho and meta positions are selectively deuterated with high levels of D incorporation. Moreover, this strategy provides an alternative way to achieve meta-C-H activation.
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.
Metal-free Semiconductor Photocatalysis for sp2 C?H Functionalization with Molecular Oxygen
Zheng, Meifang,Ghosh, Indrajit,K?nig, Burkhard,Wang, Xinchen
, p. 703 - 706 (2019)
Designing metal-free catalysts for solar energy conversion is a long-standing challenge in semiconductor photoredox catalysis (SPC). With visible-light-responsive hexagonal boron carbon nitride (h-BCN) as a non-metal photocatalyst, this system affords C?H/N?H coupling products with broad substitution tolerance and high efficiency with molecular oxygen as the terminal oxidant. The catalyst exhibits remarkable performance for the selective C?H functionalization of electron-rich arenes to C?N products (yields up to 95 %) and good stability (6 recycles). Both nitrogen heteroarenes and amine salts are competent coupling nucleophiles. Mechanically, the reactive oxygen species are superoxide anion radical (O2?.) and H2O2, which are proved by electron spin resonance (ESR) data, KI-starch, and control experiments. In addition, kinetic isotope effect (KIE) experiments indicate that C?H bond cleavage is not involved in the rate limiting step. This semiconductor-based photoredox system allows for C?H amination free of any metals, ligands, strong oxidants, and additives. It provides a complementary avenue to C?H functionalizations and enables synthetic applications efficiently in a sustainable manner.
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.).
Recyclable heterogeneous iron catalyst for C-N cross-coupling under ligand-free conditions
Swapna,Vijay Kumar,Prakash Reddy,Rama Rao
, p. 7514 - 7517 (2009)
(Chemical Equation Presented) An efficient and ligand-free C-N cross-coupling of aryl halides with various heterocycles using Fe/Cg as a recyclable catalyst is reported. The yields are excellent to moderate. 2009 American Chemical Society.
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.
Direct C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis
Chen, Bin,Chen, Ya-Jing,Cheng, Yuan-Yuan,Lei, Tao,Liang, Ge,Tung, Chen-Ho,Wang, Jing-Hao,Wu, Li-Zhu,Ye, Chen,Zhou, Chao
supporting information, p. 8082 - 8087 (2021/10/25)
An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide
