Nickel catalyzed one pot synthesis of biaryls under air at room temperature

Bhat, Aparna P. I.; Bhat, Badekai Ramachandra

doi:10.1039/c3ra43363c

Cited by 7 publications

(3 citation statements)

References 31 publications

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“…They are easily synthesized by condensing the amine group in 4-AAP with the carbonyl group attached to different aldehydes or ketones, facilitating access to a broad range of compounds with high yields. Additionally, the electron-donating nitrogen in the imine bond generates L-type ligands, capable of forming complexes with nearly any metal; − therefore, these compounds have been employed successfully in a variety of applications, including optical and nonlinear optical applications, , analytical, sensor development, solar cells, catalysis, corrosion inhibitors, organic synthesis intermediates, new drug development, , and more.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Aguilar-Llanos,

Carrera-Pacheco,

González-Pastor

et al. 2023

ACS Omega

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Eight Schiff bases, synthesized by the reaction of 4-aminoantipyrine with different cinnamaldehydes, were studied in the solid state by using vibrational spectroscopy (IR) and X-ray diffraction techniques. The analysis was extended to the solution phase through ultraviolet–vis, fluorescence spectroscopy, and cyclic voltammetry. Finally, the crystal structures of four compounds (3b, 3d, 3g, and 3h) were determined and studied. In addition to the experimental study, theoretical calculations using the semiempirical method PM6/ZDO were performed to understand better the compound’s molecular properties, UV–vis, and infrared spectra. The primary difference is the angular conformation of the terminal phenyl rings around the corresponding linking C–N and C–C σ-bonds. Furthermore, as a result of extended bonding, the > CN– azomethine group-containing Cpyr–N(CH)–(CR)(CH)–Cbz chain (with RH for 3b, 3d, and 3h, and RCH3 for 3g) is planar, nearly coplanar, with the mean plane of the pyrazole ring. Hirshfeld surface (HS) analysis was used to investigate the crystal packing and intermolecular interactions, which revealed that intermolecular C–H···O and C–H···N hydrogen bonds, π···π stacking, and C–H···π and CO···π interactions stabilize the compounds. The energy contributions to the lattice energies of potential hydrogen bonds were primarily dispersive and repulsive. All derivatives were tested in vitro on LPS-stimulated mouse macrophages to assess their ability to suppress the LPS-induced inflammatory responses. Only a slight reduction in the level of NO production was found in activated macrophages treated with 3h. Additionally, the derivatives were tested for antimicrobial activity against several clinical bacteria and fungi strains, including three biofilm-forming microorganisms. Nevertheless, only Schiff base 3f showed interesting antibacterial activities with minimum inhibitory concentration (MIC) values as low as 15.6 μM against Enterobacter gergoviae. On the other hand, Schiff base 3f and, to a lesser extent, 3b and 3h showed antifungal activity against clinical isolates of Candida. The lowest MIC value was for 3f against Candida albicans (15.6 μM). It is interesting to note that the same Schiff bases exhibit the highest activity in both biological evaluations.

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Section: Introductionmentioning

confidence: 99%

Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Aguilar-Llanos,

Carrera-Pacheco,

González-Pastor

et al. 2023

ACS Omega

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“…Hence, the development of highly efficient catalysts and the exploration of mild reaction conditions are in great demand. Even though a variety of homogeneous catalysts have been explored recently for homogeneous Ullmann coupling reactions, [8][9][10][11] the exorbitant price of the complex catalysts, non-recyclable property and complicated post-processing are still the main blocks for such a homogeneous catalysis.…”

Section: Introductionmentioning

confidence: 99%

PdAu alloy nanoparticles supported on nitrogen-doped carbon black as highly active catalysts for Ullmann coupling and nitrophenol hydrogenation reactions

et al. 2019

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“…For instance, the transition-metal-free homocoupling reactions of Grignard reagents can be effectively mediated by organic oxidants . The homocoupling of Grignard reagents has potential value for the industrial synthesis of symmetrical biaryls or polyaromatic conjugated compounds, as Grignard reagents are widely used . However, current transition-metal-free homocouplings require large amounts of the organic oxidant upward of 50 mol % .…”

mentioning

confidence: 99%

Development and Application of a Multielectron-Accepting Organic Oxidant for the Catalytic Transition-Metal-Free Oxidative Homocoupling of Grignard Reagents in Air

et al. 2015

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Nickel catalyzed one pot synthesis of biaryls under air at room temperature

Cited by 7 publications

References 31 publications

Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

Crystal Structure, Hirshfeld Surface Analysis, and Biological Activities of Schiff-Base Derivatives of 4-Aminoantipyrine

PdAu alloy nanoparticles supported on nitrogen-doped carbon black as highly active catalysts for Ullmann coupling and nitrophenol hydrogenation reactions

Development and Application of a Multielectron-Accepting Organic Oxidant for the Catalytic Transition-Metal-Free Oxidative Homocoupling of Grignard Reagents in Air

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