1821-36-9Relevant articles and documents
Synthesis and characterization of bidentate NHC-Pd complexes and their role in amination reactions
Demir, Serpil,?zdemir, Ismail,?etinkaya, Bekir,Arslan, Hakan,VanDerveer, Don
, p. 195 - 200 (2011)
The new well-defined and air-stable ortho-xylyl-linked N-heterocyclic carbene (NHC) Pd complexes (2a-d) have been synthesized and characterized by elemental analysis, 1H NMR, 13C NMR, IR spectroscopy, and single crystal X-ray diffraction studies. The palladium atom in the complex 2a lies on a crystallographic mirror plane and can be described as having a square-planar coordination environment with the carbene atoms of the benzimidazole rings of the ligand occupying two coordination sites in cis positions. Two further coordination sites are occupied by chloride ligands. The benzimidazole rings are connected to each other by an ortho-xylyl bridge. The catalytic activity of these palladium complexes has been tested in the coupling reactions of various N-containing substrates with bromobenzene. A preliminary catalytic study shows that the bis(NHC)-Pd complexes are highly active in the Buchwald-Hartwig amination reaction.
THE ACTUAL MERCURATING SPECIES IN THE MERCURATION OF AROMATIC AMINES AND THE AMINOMERCURATION OF OLEFINS
Barluenga, Jose,Bayon, Ana M.,Perez-Prieto, Julia,Asensio, Gregorio
, p. 5053 - 5062 (1984)
The reactivity of ?- and ?- N-mercurated and C-mercurated amines as electrophiles towards olefins and aromatic amines is studied under different reaction conditions.Depending on the ionic or covalent character of the starting mercury(II) salt, dissociated
ELECTROLYTIC BEHAVIOR OF TETRASUBSTITUTED IMINIUM SALT IN ACETONITRILE.
Kunai,Harada,Nishihara,Yanagi,Sasaki
, p. 2442 - 2446 (1983)
Cathodic behavior of N-cyclohexylidenepyrrolidinium salt (1) and N-cyclohexylideneaniline (2) in acetonitrile has been studied by means of dc polarography, cyclic voltammetry and preparative electrolysis under controlled potential conditions. Compound 1 e
Oxidative three-component carboamination of vinylarenes with alkylboronic acids
Gockel, Samuel N.,Lee, SangHyun,Gay, Brittany L.,Hull, Kami L.
, p. 5166 - 5171 (2021)
The three-component carboamination of alkenes is of significant interest due to the ease by which functionalized amines can be produced from readily available chemical building blocks. Previously, a variety of carbon-centered radical precursors have been
Visible-light-mediated tungsten-catalyzed C-H amination of unactivated alkanes with nitroarenes
Wang, Qing,Ni, Shengyang,Wang, Xiaochen,Wang, Yi,Pan, Yi
, p. 678 - 685 (2022/02/14)
Alkylamines are important motifs in pharmaceutical and material sciences. The existing reports of C-H amination are limited to ammonia, diazo and azide nitrogen sources. This work describes a rapid construction of C-N bonds from accessible nitroarene and alkane feedstock under decatungstate catalysis. A variety of C-H precursors including gaseous, linear, cyclic and benzylic hydrocarbons could adopt this protocol to afford the corresponding alkylamines in high efficiency. [Figure not available: see fulltext.]
Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions
Walker, Benjamin R.,Manabe, Shuhei,Brusoe, Andrew T.,Sevov, Christo S.
supporting information, p. 6257 - 6265 (2021/05/07)
Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.
Nickel?Copper bimetallic mesoporous nanoparticles: As an efficient heterogeneous catalyst for N-alkylation of amines with alcohols
Nasresfahani, Zahra,Kassaee, Mohamad Z.
, (2020/10/30)
A bimetallic catalyst (Ni/Cu-MCM-41) is prepared via co-condensation method. The latter is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), diffuse reflectance spectroscopy (DRS), and nitrogen adsorption–desorption analysis. Catalytic performance of Ni/Cu-MCM-41 is probed in N-alkylation of amines with alcohols through a hydrogen autotransfer process. Noteworthy, this catalytic system appears very efficient for synthesis of a range of secondary and tertiary amines in good to excellent isolated yields. Moreover, the catalyst is successfully recovered and reused four times without notable decrease in its activity.
