Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime

Yuan, Chunling; Zhang, Lei; Zhao, Yingdai

doi:10.3390/molecules24224177

Cited by 14 publications

(8 citation statements)

References 59 publications

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“…93%; mp 62–63 °C; 1 H NMR (600 MHz, CDCl 3 ) δ: 9.76 (s, 1H), 7.74 (d, J = 8.5 Hz, 2H), 6.99 (s, 2H), 3.41 (t, J = 5.5 Hz, 4H), 1.94–1.43 (m, 6H) matches with; IR (cm –1 ) ATR 1662; MS m / z [M + ], 189.10.…”

Section: Materials and Methodsmentioning

confidence: 99%

Synthesis and Photophysical, Electrochemical, and DFT Studies of Piperidyl and Pyrrolidinyl Chalcones

et al. 2023

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Small organic molecules with interesting optical and electrochemical properties find applications as organic luminescent materials. In this work, we report the synthesis of novel chalcones with D−A−D and D−A−D−A architecture, followed by their optical, electrochemical, and computational studies. The absorption band of these compounds occurs at 360−480 nm with emission maxima appearing around 513−552 nm. The large Stokes shifts (Δλ) for all compounds (90−132 nm) suggest intramolecular charge transfer (ICT) in the excited states. The molar absorptivity and fluorescence quantum yields were found to be in the range of 1.7−4.26 × 10 4 M −1 cm −1 and 0.29−0.39, respectively. The electrochemical parameters were determined by using cyclic voltammetry (CV). Density functional theory (DFT) calculations of all compounds were made by using B3LYP/G (d,p) functionals in chloroform and were found to have a good correlation with experimental results. Preliminary studies of absorption, photoluminescence, CV, and their theoretical correlation suggest that these compounds may be optimized for their applications in optoelectronics, sensing, and bioimaging.

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Section: Materials and Methodsmentioning

confidence: 99%

Synthesis and Photophysical, Electrochemical, and DFT Studies of Piperidyl and Pyrrolidinyl Chalcones

et al. 2023

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“…As a result, ligands that have comparable activity with Cu and that are not encumbered by IP could be valuable . One recent report from Zhao and coworkers describes the use of a benzoin oxime ligand that can promote Cu-catalyzed C–N couplings with a variety of amines . For the various applications of this Cu catalyst, 10 mol % Cu(OAc) 2 is used with 10 mol % benzoin oxime ligand in DMSO with K 3 PO 4 at 80 °C.…”

Section: Recent Reports On Cu-catalyzed C–n Couplingsmentioning

confidence: 99%

Recent Advances in Nonprecious Metal Catalysis

Singer

Monfette

Bernhardson

et al. 2020

Org. Process Res. Dev.

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Nonprecious metal catalysis is a highly active area of research for both industrial and academic laboratories. New methods that efficiently generate useful functionality in cost-effective, high yielding, and environmentally friendly ways naturally garner attention from process chemists in many different industries. This series of highlights summarizes literature on the general topic of nonprecious metal catalysis over four-month timeframes and will focus on major trends in the field that are of general interest in the pharmaceutical industry. The first installment highlights selected transformations using copper, nickel, and iron catalysts.

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“…10 One of the primary uses of arylamines is as a structural fragment for antibacterial agents (e.g., ofloxacin and pipemidic acid), antidiabetic drugs (e.g., repaglinide), nonsteroidal antiinflammatory drugs (e.g., celecoxib), and antihypertensive drugs (e.g., prazosin), among others. 11 Three prominent methods for the generation of amines are reported in the literature: S N Ar reactions, 12 classical Ullman-type coupling reactions, 13 and Buchwald-Hartwig reactions. 14,15 However,…”

mentioning

confidence: 99%

Cu/Mn-Catalyzed C–N Cross-Coupling Reaction of Aryl Chlorides and Amines Promoted by a Polyamidoamine Dendrimer

Ranjan

Varma

Kumari

et al. 2022

Synlett

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A bimetallic catalytic combinations of Mn(OAc)2 and Cu(OAc)2 was found to be significantly effective for the Buchwald type C-N cross coupling of arylchlorides and amines. Reaction is highly influenced in the presence of a promoter Poly(amidoamine) (PAMAM) dendrimer which also possesses the advantages of being stabile, non-toxic, biocompatible, non-immunogenic and acts as soluble support for transition metal complex. Although, Mn is low cost and environmentally benign, but it is not fully exploited due to its low intrinsic catalytic activity. Here, the catalytic potential of Mn was drastically increased in the presence of another metal salt (Cu(OAc)2). In bimetallic composition, Mn significantly influences the activity, selectivity and plays a vital role in catalysis. Herein, we have developed a novel, green and economical procedure for the Buchwald type C-N cross coupling of arylchlorides and amines. Presented coupling method works under aerobic and solvent-free conditions and produces an excellent yield of value-added N-arylated or alkylated products.

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Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime

Cited by 14 publications

References 59 publications

Synthesis and Photophysical, Electrochemical, and DFT Studies of Piperidyl and Pyrrolidinyl Chalcones

Synthesis and Photophysical, Electrochemical, and DFT Studies of Piperidyl and Pyrrolidinyl Chalcones

Recent Advances in Nonprecious Metal Catalysis

Cu/Mn-Catalyzed C–N Cross-Coupling Reaction of Aryl Chlorides and Amines Promoted by a Polyamidoamine Dendrimer

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