Learn more. Coordination Singularities of a Bis( Expanding the Scope of Chelating Triazolylidenes: Mesoionic Carbenes from the 1,5‐“Click”‐Regioisomer and Catalytic Synthesis of Secondary Amines from Nitroarenes. When a similar amount (20 mg, 2.1 mol % Co) of Co/NGr‐C@SiO2 was used, only 20 % of the desired pyrrole 2 was obtained (entry 3), demonstrating the advantage of the Co/NGr‐C@SiO2‐L. Next, following a reported procedure we performed a double Mannich reaction between pyrrole and a phenylpiperazine/formaldehyde mixture to obtain the desired product. Reaction conditions: 0.5 mmol nitroarene, HCOOH/TEA 5:2 mixture (1.75 mmol HCOOH, 0.7 mmol TEA), 40 mg catalyst, 100 °C, 0.8 mL 2,5‐hexanedione, 24 hours. Synthesis of biologically active pyrroles on gram scale. Ir N A similar effect on Co‐ and Fe‐catalyzed hydrogenation of nitroarenes with H2 has been observed and we postulated that base promotes heterolytic cleavage of molecular dihydrogen, generating the metal hydride species.34 As the formation of H2 as an intermediate is excluded under the reaction conditions studied, TEA must operate via a different mechanistic pathway. Open access funding enabled and organized by Projekt DEAL. or in a thesis or dissertation provided that the correct acknowledgement is given This may take some time to load. Learn about our remote access options, Leibniz-Institut für Katalyse e. V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany. Copper-Catalyzed Redox Coupling of Nitroarenes with Sodium Sulfinates. Go to our Palladium-Catalyzed Dual Ligand-Enabled Alkylation of Silyl Enol Ether and Enamide under Irradiation: Scope, Mechanism, and The-oretical Elucidation of Hybrid Alkyl Pd(I)-Radical Species. -xylyl)bis(benzimidazolylidene) Ligand and the Bis-iridium and -rhodium-Related Complexes to access the full features of the site or access our. Bond‐Forming Reactions Catalyzed by Transition Metal Complexes Bearing N‐Heterocyclic Carbene Ligands. Preparation of secondary and tertiary amines from nitroarenes and alcohols. -Substituted Nitrobenzenes with Alkylamines: A Step- and Redox-Economical Synthesis of Diazaheterocycles Expanding the Scope of Chelating Triazolylidenes: Mesoionic Carbenes from the 1,5‐“Click”‐Regioisomer and Catalytic Synthesis of Secondary Amines from Nitroarenes. Sustainable and recyclable palladium nanoparticles–catalyzed reduction of nitroaromatics in water/glycerol at room temperature. Dinuclear Tetrapyrazolyl Palladium Complexes Exhibiting Facile Tandem Transfer Hydrogenation/Suzuki Coupling Reaction of Fluoroarylketone. Iron-Catalyzed to access the full features of the site or access our, Department of Chemistry, National Taiwan University, Taipei 106, Taiwan, Instructions for using Copyright Clearance Center page. In addition, a related cobalt‐based catalyst supported on carbon (Co‐Co3O4/NGr@C) which was previously demonstrated to reduce nitroarenes to anilines10 worked well in this transformation (entry 4). o Learn more. Well dispersive Ni nanoparticles embedded in core-shell supports as efficient catalysts for 4-nitrophenol reduction. Prepared catalyst was characterized by BET‐surface area, Inductively coupled plasma atomic emission spectroscopy (ICP‐AES), X‐ray diffraction (XRD), Scanning electron microscopy (SEM), Transmission electron microscopy (TEM), Temperature programmed reduction (TPR), X‐ray photoelectron spectroscopy (XPS), Fourier transform infra‐red (FT‐IR) spectroscopy, RAMAN spectroscopy, Thermogravimetric analysis (TGA‐DTA), UV‐vis spectroscopy and Extended X‐ray absorption fine structure (EXAFS) analysis. Supported bimetallic nano-alloys as highly active catalysts for the one-pot tandem synthesis of imines and secondary amines from nitrobenzene and alcohols. Catalyst recycling test: synthesis of 19. Thus, in the desired catalytic material, metal nanoparticles should be located on an acidic support. Synthesis of biaryls via the Suzuki–Miyaura coupling (SMC) reaction using nitroarenes as an electrophilic coupling partners is described. Visible‐Light‐Driven Selective Oxidative Coupling of Amines to Imines by Bismuth‐Rich Bismuth Oxybromide in Water. Coordination and space confined preparation of nickel sub-nanoparticles within a metal-organic framework for catalytic degradation of methyl orange. Heterometallic complexes, tandem catalysis and catalytic cooperativity. . Addressing the limitations of the methodology described above, we developed an improved N‐aryl pyrrole synthesis from nitroarenes using HCOOH‐Et3N as an alternative to molecular hydrogen (Scheme 4). -Substituted Nitrobenzenes with Alkylamines: A Step- and Redox-Economical Synthesis of Diazaheterocycles Palladium-catalyzed N-arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes. One-pot synthesis of imines from benzyl alcohol and amines on Au/ZrO2 catalyst. Heterobimetallic Complexes as Catalysts for the Coupling of Nitrobenzene and Benzylic Alcohol For reproduction of material from all other RSC journals and books: For reproduction of material from all other RSC journals. Similarly, ethyl cinnamate containing pyrrole 14 was obtained without any products of C=C bond hydrogenation. do not need to formally request permission to reproduce material contained in this Intermetallic Ni Superior activity of 4.9% Ni‐ZrO2 was due to presence of very small (below 5 nm), uniformly distributed, highly dispersed nickel nanoparticle having good metal‐support interaction. Nitroarenes bearing electron‐rich substituents are well‐tolerated under standard reaction conditions, as shown with pyrroles 7 and 8. In fact, the avoidance of separation steps and isolation of intermediates offers significant economic and environmental benefits. E-mail: We have developed a heterogeneous Co/NGr‐C@SiO2‐L catalyst for an efficient cascade synthesis of pyrroles starting from the corresponding nitroarenes using either hydrogen or formic acid or CO/H2O mixtures as reducing agents. Working off-campus? In Japan, all five listed nitroarenes were detected in particulates derived from coal burning (Taga et al. Direct one-pot reductive imination of nitroarenes using aldehydes and carbon monoxide by titania supported gold nanoparticles at room temperature. Catalytic evaluation of tunable Ni nanoparticles embedded in organic functionalized 2D and 3D ordered mesoporous silicas from the hydrogenation of nitroarenes.