scholarly journals Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1120
Author(s):  
Giuseppe Romanazzi ◽  
Valentina Petrelli ◽  
Ambra Maria Fiore ◽  
Piero Mastrorilli ◽  
Maria Michela Dell’Anna

Recently, N-substituted anilines have been the object of increasing research interest in the field of organic chemistry due to their role as key intermediates for the synthesis of important compounds such as polymers, dyes, drugs, agrochemicals and pharmaceutical products. Among the various methods reported in literature for the formation of C–N bonds to access secondary anilines, the one-pot reductive amination of aldehydes with nitroarenes is the most interesting procedure, because it allows to obtain diverse N-substituted aryl amines by simple reduction of nitro compounds followed by condensation with aldehydes and subsequent reduction of the imine intermediates. These kinds of tandem reactions are generally catalyzed by transition metal-based catalysts, mainly potentially reusable metal nanoparticles. The rapid growth in the last years in the field of metal-based heterogeneous catalysts for the one-pot reductive amination of aldehydes with nitroarenes demands for a review on the state of the art with a special emphasis on the different kinds of metals used as catalysts and their recyclability features.

Catalysts ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 287
Author(s):  
Jianguo Liu ◽  
Mingyue Zhang ◽  
Longlong Ma

Dibenzylamine motifs are an important class of crucial organic compounds and are widely used in fine chemical and pharmaceutical industries. The development of the efficient, economical, and environmentally friendly synthesis of amines using transition metal-based heterogeneous catalysts remains both desirable and challenging. Herein, we prepared the covalent organic framework (COF)-supported heterogeneous reduced COF-supported Pd-based catalyst and used it for the one-pot reductive amination of aldehydes. There are both Pd metallic state and oxidated Pdσ+ in the catalysts. Furthermore, in the presence of the reduced COF-supported Pd-based catalyst, many aromatic, aliphatic, and heterocyclic aldehydes with various functional groups substituted were converted to their corresponding amines products in good to excellent selectivity (up to 91%) under mild reaction conditions (70 °C, 2 h, NH3, 20 bar H2). This work expands the covalent organic frameworks for the material family and its support catalyst, opening up new catalytic applications in the economical, practical, and effective synthesis of secondary amines.


2018 ◽  
Vol 43 (3-4) ◽  
pp. 286-299 ◽  
Author(s):  
Osman Asheri ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Mehdi Shahraki

The kinetics of the reaction between para-substituted anilines and dimethyl acetylenedicarboxylate (DMAD) with derivatives of benzaldehyde for the one-pot formation of 3,4,5-substituted furan-2(5 H)-ones in the presence of lactic acid as a catalyst have been studied spectrophotometrically at different temperatures. A mechanism involving four steps was proposed for the reactions, all of which followed second-order kinetics. The partial orders with respect to substituted aniline and DMAD were one and one and the reactions revealed zero-order kinetics for benzaldehyde and its derivatives. Changing of substituents on benzaldehyde left rates of reaction unaffected. However, various substituents on aniline showed that para electron-withdrawing groups decreased the rate of reaction. According to investigation of an isokinetic relationship, a common mechanism exists for all studied substituents and a general mechanism can be formulated. Kinetic values ( k and Ea) and associated activation parameters (Δ G‡, Δ S‡ and Δ H‡) of the reactions were determined.


2009 ◽  
Vol 11 (2) ◽  
pp. 265-268 ◽  
Author(s):  
Laura Rubio-Pérez ◽  
F. Javier Pérez-Flores ◽  
Pankaj Sharma ◽  
Luis Velasco ◽  
Armando Cabrera

2020 ◽  
Vol 7 (1) ◽  
pp. 82-90 ◽  
Author(s):  
Xiao Chen ◽  
Shuhua Han ◽  
Dongdong Yin ◽  
Changhai Liang

For the one-pot reductive amination of benzaldehyde with nitrobenzene, intermetallic Ni2Si/SiCN from the decomposition of a nickel-modified polysilazane precursor exhibited high activity (>99%) and high selectivity (92% to aromatic amine).


2020 ◽  
Vol 10 (13) ◽  
pp. 4201-4209
Author(s):  
Jin Hee Cho ◽  
Sangmoon Byun ◽  
Ahra Cho ◽  
B. Moon Kim

We have developed a new catalytic method for the one-pot, cascade synthesis of unsymmetrical secondary amines via the reductive amination of aryl nitriles with nitroalkanes using a PdPt–Fe3O4 nanoparticle (NP) catalyst.


2020 ◽  
Vol 10 (12) ◽  
pp. 3918-3930 ◽  
Author(s):  
Jaqueline F. Souza ◽  
Thalita F. B. de Aquino ◽  
José E. R. Nascimento ◽  
Raquel G. Jacob ◽  
André R. Fajardo

This study demonstrates the facile preparation and use of alginate–Cu2+ microspheres in the catalysis of a new class of organoselenium substituted pyrazoles through one-pot reactions.


RSC Advances ◽  
2016 ◽  
Vol 6 (101) ◽  
pp. 99604-99614 ◽  
Author(s):  
Madhvi Bhardwaj ◽  
Manmeet Kour ◽  
Satya Paul

Bifunctional heterogeneous catalysts based on Cu(0) onto sulphonated silica/carbon composites for the one-pot synthesis of polysubstituted pyridines and oxidative transformation of aldehydes to nitriles.


ChemInform ◽  
2011 ◽  
Vol 42 (20) ◽  
pp. no-no ◽  
Author(s):  
Maria J. Climent ◽  
Avelino Corma ◽  
Sara Iborra

Author(s):  
Enrico Catizzone ◽  
Giuseppe Bonura ◽  
Massimo Migliori ◽  
Francesco Frusteri ◽  
Girolamo Giordano

Starting from the environmental issues related to global warming, climate change and reduction of greenhouse gas emissions, this review paper describes how CO2 recycling can represent a challenging strategy suitable to explore new concepts and opportunities for catalytic and industrial development. In this view, the production of dimethyl ether (DME) from catalytic hydrogenation of CO2 appears as a viable technology, able to meet also the ever-increasing need for alternative environmentally-friendly fuels and energy carriers. Basic considerations on thermodynamic aspects controlling DME production from CO2 are presented, then summarizing the main catalytic systems developed in such a field. Special attention is paid on the role assumed during last years by zeolite-based systems, either in the methanol-to-DME dehydration step or in the one-pot CO2-to-DME hydrogenation. On the whole, the productivity of DME results significantly to be dependent on several catalyst features, linked not only to the metal-oxide phase responsible for CO2 activation/hydrogenation, but also to specific properties of the zeolites (i.e., topology, porosity, surface area, acidity, interaction with active metals, distributions of metal particles, …) influencing activity and stability of hybridized bifunctional heterogeneous catalysts.


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