1205-39-6Relevant articles and documents
Visible light-driven cross-coupling reactions at lower temperatures using a photocatalyst of palladium and gold alloy nanoparticles
Xiao, Qi,Sarina, Sarina,Bo, Arixin,Jia, Jianfeng,Liu, Hongwei,Arnold, Dennis P.,Huang, Yiming,Wu, Haishun,Zhu, Huaiyong
, p. 1725 - 1734 (2014)
Palladium (Pd)-catalyzed cross-coupling reactions are among the most important methods in organic synthesis. We report the discovery of highly efficient and green photocatalytic processes by which cross-coupling reactions, including Sonogashira, Stille, Hiyama, Ullmann, and Buchwald-Hartwig reactions, can be driven with visible light at temperatures slightly above room temperature using alloy nanoparticles of gold and Pd on zirconium oxide, thus achieving high yields. The alloy nanoparticles absorb visible light, and their conduction electrons gain energy, which is available at the surface Pd sites. Results of the density functional theory calculations indicate that transfer of the light excited electrons from the nanoparticle surface to the reactant molecules adsorbed on the nanoparticle surface activates the reactants. When the light intensity was increased, a higher reaction rate was observed, because of the increased population of photoexcited electrons. The irradiation wavelength also has an important impact on the reaction rates. Ultraviolet irradiation can drive some reactions with the chlorobenzene substrate, while visible light irradiation failed to, and substantially improve the yields of the reactions with the bromobenzene substrate. The discovery reveals the possibility of using low-energy and -density sources such as sunlight to drive chemical transformations.
Palladium-catalyzed one-pot diarylamine formation from nitroarenes and cyclohexanones
Xie, Yanjun,Liu, Saiwen,Liu, Yong,Wen, Yuqing,Deng, Guo-Jun
, p. 1692 - 1695 (2012)
The first palladium-catalyzed diarylamine formation from nitroarenes and cyclohexanone derivatives using borrowed hydrogen is described. Various diarylamines were selectively obtained in good to excellent yields. The reaction tolerated a wide range of functionalities. The nitro reduction, cyclohexanone dehydrogenation, and imine formation and reduction were realized in a cascade without an external reducing reagent and oxidant.
Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions
Hu, Huaiyuan,Gilliam, Ashley M.,Qu, Fengrui,Shaughnessy, Kevin H.
, p. 4127 - 4135 (2020)
Enolizable ketones have been identified as effective activators for palladium(II) precatalysts in the coupling of aryl bromides and aniline. N-arylation reactions catalyzed by [(DTBNpP)PdCl2]2 (DTBNpP = (bis(tert-butyl)neopentylphosphine) and PEPPSI-IPr precatalysts are activated by the addition of acetone, mesityl oxide, and 3-pentanone. 3-Pentanone was the most effective activator. Mechanistic studies show that acetone, 3-pentanone, and mesityl oxide reduce [(DTBNpP)PdCl2]2 in the presence of NaO-t-Bu to Pd0(DTBNpP)2
Pentavalent organoantimony compounds as mild N-arylating agents for amines: Cu-mediated ullmann-type N-arylation with tetraarylantimony(V) acetates
Qin, Weiwei,Kakusawa, Naoki,Wu, Yichen,Yasuike, Shuji,Kurita, Jyoji
, p. 436 - 438 (2009)
Simple and mild Cu-mediated arylation of various amines by use of tetraarylantimony acetate (Ar4SbOAc) is described. The Ullmann-type condensation of Ar4SbOAc with aliphatic and electron rich aromatic amines proceeded efficiently in
3-(Diphenylphosphino)propanoic acid: An efficient ligand for Cu-catalyzed N-arylations of indoles and aryl amines
Liu,Gu,Liu,Ma,Liu,Xie
, p. 1075 - 1078 (2015)
3-(Diphenylphosphino)propanoic acid (L2) was found to be an efficient ligand for the copper-catalyzed N-arylations of indoles and arylamines with aryl iodides, the C-N coupling reactions catalyzed by CuCl/L2 were smoothly carried out in DMSO at 120 °C and give the corresponding products with the yields of 25-98 %.
Stable, Well-Defined Nickel(0) Catalysts for Catalytic C-C and C-N Bond Formation
Nett, Alex J.,Canellas, Santiago,Higuchi, Yuki,Robo, Michael T.,Kochkodan, Jeanne M.,Haynes, M. Taylor,Kampf, Jeff W.,Montgomery, John
, p. 6606 - 6611 (2018)
The synthesis and catalytic activity of several classes of NHC-Ni(0) precatalysts stabilized by electron-withdrawing alkenes are described. Variations in the structure of fumarate and acrylate ligands modulate the reactivity and stability of the NHC-Ni(0) precatalysts and lead to practical and versatile catalysts for a variety of transformations. The catalytic activity and efficiency of representative members of this class of catalysts have been evaluated in reductive couplings of aldehydes and alkynes and in N-arylations of amines.
Aromatic Substitution by Phenylnitrenium and Naphthylnitrenium Ions formed from Phenyl Azide and 1-Azidonaphthalene in the Presence of Trifluoromethanesulphonic Acid
Takeuchi, Hiroshi,Takano, Katsuyuki
, p. 447 - 449 (1983)
Aromatic N-substitution by phenylnitrenium ions generated from phenyl azide in the presence of a catalytic amount of trifluoromethanesulphonic acid gave diarylamines (in especially good yield in the reaction with biphenyl or naphthalene), whereas naphthylnitrenium ions from 1-azidonaphthalene react with benzene to afford a C-substitution product, 1-amino-4-phenylnaphthalene.
High Catalytic Activity of Peptide Nanofibres Decorated with Ni and Cu Nanoparticles for the Synthesis of 5-Substituted 1H-Tetrazoles and N-Arylation of Amines
Ghorbani-Choghamarani, Arash,Taherinia, Zahra
, p. 1127 - 1137 (2017)
A rapid development of a new methodology for decarboxylative N-arylation of carboxylic acids and the preparation of 5-substituted 1H-tetrazoles catalysed by peptide nanofibres decorated with Cu and Ni nanoparticles is presented. Compared with conventional aryl halides, benzoic acids are extremely interesting and environmentally friendly options for the synthesis of secondary aryl amines.
N-Heterocyclic Carbene Palladium(II) Amine Complexes: The Role of Primary Aryl- or Alkylamine Binding and Applications in the Buchwald-Hartwig Amination Reaction
Hsu, Yu-Cheng,Chen, Ming-Tsz
supporting information, (2021/12/24)
N-heterocyclic carbene-palladium(II) amine complexes bearing primary aryl- or alkylamines were synthesized. The prepared complexes were characterized by single crystal X-ray diffraction as well as NMR spectroscopy. These complexes exhibited good catalytic activities for the Buchwald-Hartwig amination reaction of aryl chlorides to afford arylated anilines under mild conditions. All reactions were carried out in air and all starting materials were used as supplied without purification. 21 expected coupling products were obtained in moderate to high yields under optimum conditions.
Chitosan nanoparticles functionalized poly-2-hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N-arylation of amines with phenylboronic acid at ambient temperature
Seyedi, Neda,Zahedifar, Mahboobeh
, (2021/07/25)
The present study aims to prepare an effective and eco-friendly nanocatalyst for the Chan–Lam coupling reaction of phenylboronic acid and amine in aerobic conditions. For this purpose, chitosan was extracted from shrimp shells waste by demineralization, deproteinization, and deacetylation processes and then converted to chitosan nanoparticles (CSN) by the ionic gelation with tripolyphosphate anions. Afterward, poly-2-hydroxyaniline (P2-HA) was grafted to chitosan nanoparticles (NPs) to employ as the support for CuO NPs. Characterization of the nanocatalyst was done using Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), mapping, energy-dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA). The CuO NPs were identified in the spherical shape with an average size of 17 nm. The prepared nanocatalyst exhibited excellent catalytic performance with a high turnover number (TON) and turnover frequency (TOF) for the Chan–Lam coupling reaction of phenyl boronic acid and amines with different electronic properties. The prepared catalyst could be readily recovered and reused for at least five runs without any noticeable change in structure and catalytic performance. Chitosan (CS) was prepared via demineralization, deproteinization, and deacetylation of shrimp shell and chitosan nanoparticles (CSN) were prepared via ionic gelation process. Polymerization of 2-HA on the CSN surface was done to increase functional groups and create active sites for CuO NPs attachments. CuO NPs-P2-HA-CSN nanocomposite has been shown high efficiently for the Chan–Lam coupling reaction.
Nitrogen-containing compound, organic electroluminescent device, and electronic device
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Paragraph 0111-0117, (2021/01/24)
The invention provides a nitrogen-containing compound, an organic electroluminescent device and an electronic device, and belongs to the technical field of organic materials. The structure of the nitrogen-containing compound is represented by Chemical Formula 1: wherein X1, X2, Y1, Y2 are the same or different from each other and are each independently a single bond, O, S, N(R3), C(R4R5), Ge(R6R7), Si(R8R9), Se, wherein X1 and Y1 are not single bonds simultaneously and X2 and Y2 are not single bonds simultaneously.
