102904-37-0Relevant articles and documents
A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction-carbonylation of nitroarenes
Sobhani, Sara,Chahkamali, Farhad Omarzehi,Sansano, José Miguel
, p. 1362 - 1372 (2019)
In this work, synthesis of Pd-NHC-γ-Fe2O3-n-butyl-SO3H and its activity as a bifunctional heterogeneous nanocatalyst containing Pd-NHC and acidic functional groups, are described. This newly synthesized nanomagnetic catalyst is fully characterized by different methods such as FT-IR, XPS, TEM, VSM, ICP and TG analysis. At first, the catalytic activity of Pd-NHC-γ-Fe2O3-n-butyl-SO3H is evaluated for the reduction of nitroarenes in aqueous media using NaBH4 as a clean source of hydrogen generation at ambient temperature. Using the promising results obtained from the nitroarene reduction, this catalytic system is used for two one-pot protocols including reduction-Schiff base condensation and reduction-carbonylation of various nitroarenes. In these reactions the in situ formed amines are further reacted with aldehydes to yield imines or carbonylated to amides. The desired products are obtained in good to high yields in the presence of Pd-NHC-γ-Fe2O3-n-butyl-SO3H as a bifunctional catalyst. The catalyst is reused with the aid of a magnetic bar for up to six consecutive cycles without any drastic loss of its catalytic activity.
Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation
Cardinale, Luana,Schmotz, Mattis-Ole W. S.,Konev, Mikhail O.,Jacobi von Wangelin, Axel
supporting information, p. 506 - 510 (2022/01/20)
An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.
Nanomagnetic catalysis (Fe3O4@S–TiO2): a novel magnetically nano catalyst for the synthesis of new highly substituted tetrahydropyridine derivatives under solvent-free conditions
Nezami, Zahra,Eshghi, Hossein
, p. 1997 - 2008 (2021/01/20)
A novel nanomagnetic catalyst (Fe3O4@S–TiO2) was prepared by the hydrothermal method. At the first, Fe3O4 nanoparticles were synthesized, then iron oxide nanoparticles (IONPs) were dispersed in ethano
Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams
Ye, Jian-Heng,Bellotti, Peter,Paulisch, Tiffany O.,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 13671 - 13676 (2021/05/11)
We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
supporting information, (2020/06/17)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ
Xiong, Ruimei,Hussain, Muhammad Ijaz,Liu, Qing,Xia, Wen,Xiong, Yan
supporting information, (2019/12/11)
A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.
Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media
Nasseri, Mohammad Ali,Ramezani-Moghadam, Simin,Kazemnejadi, Milad,Allahresani, Ali
, p. 4233 - 4256 (2020/07/08)
Abstract: A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity. Graphic abstract: A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni nanocatalyst.[Figure not available: see fulltext.]
Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin
Bauri, Somnath,Pandey, Vipin K.,Rit, Arnab
supporting information, p. 3853 - 3857 (2020/07/27)
A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is
Retraction: Harnessing Thiol as a Benzyl Reagent for Photocatalytic Reductive Benzylation of Imines (Organic Letters DOI: 10.1021/2Facs.orglett.0c00065)
Zhang, Jinghui,Zhang, Muliang
supporting information, p. 2112 - 2112 (2020/02/15)
The authors retract this article after finding in subsequent studies that the quality of the purchased catalysts has a notable impact on the reproducibility of the results. Accordingly, the authors note that additional work is necessary to understand the
Mild and efficient synthesis of secondary aromatic amines by one-pot stepwise reductive amination of arylaldehydes with nitroarenes promoted by reusable nickel nanoparticles
Fiore, Ambra Maria,Romanazzi, Giuseppe,Dell'Anna, Maria Michela,Latronico, Mario,Leonelli, Cristina,Mali, Matilda,Rizzuti, Antonino,Mastrorilli, Piero
, (2019/07/31)
The one-pot stepwise reductive amination of arylaldehydes with nitroarenes is described, using reusable nickel nanoparticles (Ni-pol) as catalyst and NaBH4 as mild, inexpensive, and safe reducing agent. The proposed catalytic system holds several advantages such as the use of a non-precious and earth-abundant metal, the facile separation of the catalyst from the reaction mixture by centrifugation, excellent stability towards air and moisture, very mild reaction conditions, good recyclability, broad substrate scope with good to excellent yields, and easy scalability (up to 1.0 g). FESEM analyses indicate that the active species are cubic nanocrystals of Ni in the average cross section value of 35 nm with a quite narrow (25–45 nm) and monomodal distribution, which becomes bimodal with the recycling reactions but without agglomeration.
