101-17-7Relevant articles and documents
Practical copper-catalyzed N-arylation of amines with 20% aqueous solution of n-Bu4NOH
Molaei, Hamidreza,Ghanbari, Mohammad Mehdi
, p. 301 - 304 (2012)
N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20% aqueous solution of n-Bu4NOH was accomplished in good to excellent yields (up to 92%) and substrate conversions (up to 96%).
Visible-Light-Mediated Chan-Lam Coupling Reactions of Aryl Boronic Acids and Aniline Derivatives
Yoo, Woo-Jin,Tsukamoto, Tatsuhiro,Kobayashi, Shu
, p. 6587 - 6590 (2015)
The copper(II)-catalyzed aerobic oxidative coupling reaction between aryl boronic acids and aniline derivatives was found to be improved significantly under visible-light-mediated photoredox catalysis. The substrate scope of this oxidative Chan-Lam reaction was thus expanded to include electron-deficient aryl boronic acids as viable starting materials. Two are better than one: The copper(II)-catalyzed aerobic oxidative coupling reaction between aryl boronic acids and anilines is significantly improved by the addition of visible-light-mediated photoredox catalysts. The substrate scope of this Chan-Lam reaction was thus expanded to include electron-deficient aryl boronic acids.
Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling
Kumari, Kavita,Kumar, Saurabh,Singh, Krishna Nand,Drew, Michael G. B.,Singh, Nanhai
, p. 12143 - 12153 (2020)
Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is
Imidazole-directed fabrication of three polyoxovanadate-based copper frameworks as efficient catalysts for constructing C-N bonds
Gong, Shuwen,Gu, Yuxiao,Huang, Xianqiang,Li, Jikun,Li, Qiang,Qi, Yuquan,Shen, Guodong
, p. 10970 - 10976 (2020)
A synthetic pathway for the directed preparation of three novel polyoxovanadate-based copper frameworks (POVCFs), i.e., [Cu0.5(1-ipIM)2]2[V4O11] (POVCF 1), [Cu(1-ipIM)2](VO3)2 (POVCF 2) and [Cu(1-pIM)4](HpIM)4[V10O28] (POVCF 3) (1-ipIM = 1-isopropylimidazole; 1-pIM = 1-propylimidazole) using bifunctional imidazole molecules as organic ligands and base has been developed. Systematic studies revealed that the variable base enviroment in the reaction is the key step in the preparation of 1D to 3D supermolecular networks of POVCFs 1-3. Single crystal X-ray diffraction analyses demonstrated that the Cu2+ atoms of POVCFs 1-2 were coordinated with four imidazole derivative molecules and two different polyoxovanadate {[V4O11]2- and [V10O28]6-} clusters, respectively, exhibiting a [CuN4O2] binding set and a distorted octahedral geometry. Specifically, POVCF 1 exhibited adjacent [V4O11]2- that dangle up and down arranged in a parallel 2D network and further coordinated with [Cu(1-ipIM)4]2+ to form a 3D supramolecular structure. However, POVCF 3 presented one tetrahedral coordinated vanadium atom and one four-coordinated copper atom and they further gave rise to a 1D network by the Cu-O and V-O bonds. More importantly, these POVCFs were further studied in the construction of C-N bond reactions of primary amines under mild conditions, and it was found that POVCF 1 displayed efficient heterogeneous catalytic activities in the Chan-Lam reaction (yields up to 89%). This journal is
Electrochemically Enabled Chan-Lam Couplings of Aryl Boronic Acids and Anilines
Wexler, Ryan P.,Nuhant, Philippe,Senter, Timothy J.,Gale-Day, Zachary J.
, p. 4540 - 4543 (2019)
The Chan-Lam reaction remains a highly utilized transformation for C-N bond formation. However, anilines remain problematic substrates due to their lower nucleophilicity. To address this problem, we developed an electrochemically mediated Chan-Lam coupling of aryl boronic acids and amines utilizing a dual copper anode/cathode system. The mild conditions identified have enabled the preparation of a wide range of functionalized biarylanilines in good yields and chemoselectivities.
Design, preparation and characterization of aerogel NiO-CuO-CoO/SiO2 nanocomposite as a reusable catalyst for C-N cross-coupling reaction
Ghasemi, Amir Hossein,Naeimi, Hossein
, p. 5056 - 5063 (2020)
Aerogels are porous, non-crystalline solid materials with high specific surface space, plentiful three-dimensional (3D) porous construction, ultra-low density and significant porosity. The aerogel nanocomposite is produced using sol-gel and supercritical drying processes. CO2 supercritical drying (SCD) is the most powerful process, ensuring optimal product properties such as high porosity, low density, and high thermal conductivity. On this account, we used the CO2 supercritical drying method to produce NiO-CuO-CoO/SiO2 nanocomposite aerogels and applied it as a reusable catalyst for the C-N cross-coupling reaction (Buchwald-Hartwig amination). Powerful catalytic activity for the C-N cross-coupling reaction was obtained for the new nanocomposite aerogel, that is, NiO-CuO-CoO/SiO2. The catalyst was characterized by X-ray Powder Diffraction (XRD), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDS), elemental mapping and Brunauer-Emmett-Teller (BET). Also, organic compounds were identified by melting point, Fourier-transform infrared spectroscopy (FT-IR) and hydrogen-1 nuclear magnetic resonance (1H NMR) analyses.
N-arylation of amines with o-silylaryl triflate
Lee,Jung,Hahn
, p. 6690 - 6692 (2013)
An efficient, transition-metal-free procedure for the N-arylation of amines 1 has been achieved by allowing those substrates to react with o-silylaryl triflate 2 in the presence of CsF. Good to excellent yields of arylated products 3 are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.
Metal-free synthesis of secondary amines by the reaction of tosyl triazene and aryl boronic acid
Sarma, Manas Jyoti,Phukan, Prodeep
, p. 656 - 662 (2018)
A metal free noncatalytic amination process has been developed for the synthesis of N-substituted aniline using a new amine source. The amine source p-toluene sulfonyl triazene (PhN?NNHTs) has been prepared by treating aryldiazonium salt with p-tosylamide. Various unsymmetrical amines could be synthesized by treating this reagent and boronic acid in toluene at 110 °C in the presence of DBU and 4 ? molecular sieve. A large variety of N-substituted aniline could be synthesized with moderate yield.
Novel boron compounds and Organic light emitting diode including the same
-
Paragraph 0361; 0370-0373, (2021/02/02)
The present invention relates to a boron compound usable in an organic light-emitting device, and an organic light-emitting device comprising the same and, more particularly, to a boron compound represented by any one of chemical formula A to chemical formula D and an organic light-emitting device comprising the same. The chemical formula A to chemical formula D are the same as described in the detailed description of the invention. When the novel boron compound is used as a dopant material in an organic light-emitting device, the organic light-emitting device exhibits longer life characteristics compared to the prior art.
Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature
Manna, Kartic,Ganguly, Tanusree,Baitalik, Sujoy,Jana, Ranjan
supporting information, p. 8634 - 8639 (2021/11/01)
We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.
