25373-49-3Relevant academic research and scientific papers
Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles
Edjoc, Racquel K.,Mills, L. Reginald,Rousseaux, Sophie A. L.
supporting information, p. 10422 - 10428 (2021/07/26)
The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles.
Magnetically retrievable lepidocrocite supported copper oxide nanocatalyst (Fe-CuO) for N-arylation of imidazole
Sivakami,Babu, S. Ganesh,Dhanuskodi,Karvembu
, p. 8571 - 8578 (2015/03/03)
A simple and efficient lepidocrocite-supported copper oxide catalyst (Fe-CuO) has been successfully prepared by a simple precipitation method in aqueous medium from readily available inexpensive starting materials and was used as a heterogeneous nanocatal
Cu(0)@Al2O3/SiO2 NPs: An efficient reusable catalyst for the cross coupling reactions of aryl chlorides with amines and anilines
Reddy, P. Linga,Arundhathi,Rawat, Diwan S.
, p. 92121 - 92127 (2015/11/17)
The C-N cross coupling reaction of aryl chlorides with various alkyl/aryl amines catalyzed by copper nanoparticles impregnated on alumina/silica support (Cu(0)@Al2O3/SiO2) was investigated. The prepared catalyst was characterized for its intrinsic physico-chemical and textural properties using XRD, XPS, HR-TEM, BET surface area, SEM-EDAX, H2-TPR and ICP-AES techniques. The catalyst exhibits excellent reactivity and efficacy in the cross-coupling of a wide range of alkyl/aryl amines including challenging anilines with aryl chlorides. The catalyst offers significant advantages such as brevity, milder reaction conditions, excellent yields and high functional group tolerance for C-N cross coupling when compared with the other reported methods. Moreover, this atom-economical methodology does not require an additional ligand or co-catalyst/activator. The Cu(0)@Al2O3/SiO2 catalyst was efficiently applied to a gram scale synthesis of 7-chloro-4-(4-(2-nitrophenyl)piperazin-1-yl)quinolone (2k). The robustness of the catalyst was examined by reusing it for five consecutive runs.
Cheap Cu(I)/hexamethylenetetramine (HMTA) catalytic system for C-N coupling reactions
Cao, Changsheng,Lu, Zhongbo,Cai, Zhengyuan,Pang, Guangsheng,Shi, Yanhui
experimental part, p. 279 - 284 (2011/10/31)
An efficient C-N coupling reaction of aryl chlorides or bromides with imidazole was successfully performed with cheap and commercially available catalytic system Cu(I)/HMTA. Both aryl bromides and aryl chlorides have been effectively catalyzed by Cu/HMTA, giving products in moderate to good yields. Moreover, aryl halides bearing either electron-withdrawing groups or electron-donating groups could be used in the reaction. Taylor & Francis Group, LLC.
Mild transition-metal-free amination of fluoroarenes catalyzed by fluoride ions
Dehe, Daniel,Munstein, Isabel,Reis, Andreas,Thiel, Werner R.
experimental part, p. 1151 - 1154 (2011/05/02)
Trimethylsilyl-protected heterocycles undergo N-C bond formation with a variety of electron-deficient fluoroarenes catalyzed by fluoride ions. This reaction avoids stoichiometric amounts of base and thus makes N-arylheterocycles accessible in a very mild and transition-metal-free way.
Cu-Al hydrotalcite: An efficient and reusable ligand-free catalyst for the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines
Sreedhar,Arundhathi,Linga Reddy,Amarnath Reddy,Lakshmi Kantam
experimental part, p. 2517 - 2522 (2010/03/24)
Copper-aluminum hydrotalcite catalysts were effectively used in the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines to afford the corresponding N-alkylated/arylated amines in excellent yields. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles with almost consistent activity. Georg Thieme Verlag Stuttgart.
CuI nanoparticles for C-N and C-O cross coupling of heterocyclic amines and phenols with chlorobenzenes
Sreedhar,Arundhathi,Reddy, P. Linga,Kantam, M. Lakshmi
supporting information; experimental part, p. 7951 - 7954 (2010/01/16)
(Chemical Equation Presented) Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields. 2009 American Chemical Society.
N-arylation of heterocycles with chloro- and fluoroarenes using resin-supported sulfonato-Cu(salen) complex
Kantam, M. Lakshmi,Ramani,Chakrapani
, p. 626 - 636 (2008/04/12)
Sulfonato-Cu(salen) complex immobilized onto a Merrifield's resin was found to be an efficient catalyst for the N-arylation of heterocycles with electron-withdrawing hloro- and fluoroarenes. The reactions were carried out in the presence of an inexpensive mild base, K2CO3, and N-arylated compounds were obtained in good to excellent yields. The catalyst was recovered by simple filtration and reused for three cycles with almost consistent activity. Copyright Taylor & Francis Group, LLC.
Bis(μ-iodo)bis((-)-sparteine)dicopper(I): versatile catalyst for direct N-arylation of diverse nitrogen heterocycles with haloarenes
Maheswaran,Krishna, G. Gopi,Prasanth, K. Leon,Srinivas,Chaitanya, G. Krishna,Bhanuprakash
, p. 2471 - 2479 (2008/09/18)
The easy-to-prepare dimeric bis(μ-iodo)bis((-)-sparteine)dicopper(I) complex is shown to be a versatile catalyst for N-arylation of number of NH-heterocycles with structurally divergent aryl halides including activated aryl chloride substrates under mild conditions. The DFT studies not only provide structural insights into square-pyramidal Cu(III) intermediate complexes derived from (-)-sparteine, but also highlight the important role of sterically demanding (-)-sparteine ligand framework in promoting activation of aryl-chlorine bonds for N-arylation of imidazoles.
Copper(I) thiophene-2-carboxylate (CuTC): A versatile non-nitrogen ligand-based catalyst for direct N-arylation of imidazole and pyrazole using aryl iodides, aryl bromides, and aryl chlorides
Maheswaran, Hariharasarma,Krishna, Gaddamanugu Gopi,Srinivas, Vandanapu,Prasanth, Kurushunkal Leon,Rajasekhar, Chinamukthevi Venkata
supporting information; experimental part, p. 515 - 517 (2009/04/10)
A new protocol to prepare N-aryl heterocyclic adducts in excellent yields via cross-coupling of HN-heterocycles with aryl halides is reported using commercially available and easy-to-prepare copper(I) thiophene-2-carboxylate (CuTC) as catalyst.
