1029598-42-2Relevant articles and documents
Selective synthesis of nitroalcohols in the presence of Ambersep 900 OH as heterogeneous catalyst
Lodh, Rajsekhar,Sarma, Manas Jyoti,Borah, Arun Jyoti,Phukan, Prodeep
, p. 969 - 972 (2015)
Abstract A green protocol has been developed for the selective synthesis of β-nitroalcohols using commercially available Ambersep 900 OH as reusable heterogeneous catalyst. The reaction between aldehyde and nitromethane was performed under solvent-free condition at room temperature within a short time (70-150 min) in the presence of 10 wt % of Ambersep 900 OH to produce corresponding nitroalcohols in high yield (72-91 %). After the reaction is over, the catalyst can be separated and reused (3 cycles) without appreciable loss in its activity.
A three-dimensional (3D) manganese (II) coordination polymer: Synthesis, structure and catalytic activities
Pal, Souvik,Maiti, Sudip,Nayek, Hari Pada
, (2018)
A new Mn (II)-containing coordination polymer, [Mn6(Ipa)6(ad)?6H2O] (1; Ipa?=?isophthalate ligand; ad?=?adenine), was synthesized by reacting hydrated manganese nitrate with isophthalic acid and adenine under solvothermal
High-nitrogen containing covalent triazine frameworks as basic catalytic support for the Cu-catalyzed Henry reaction
Tahir, Norini,Wang, Guangbo,Onyshchenko, Iuliia,De Geyter, Nathalie,Leus, Karen,Morent, Rino,Van Der Voort, Pascal
, p. 242 - 248 (2019)
Functionalization of porous organic frameworks by a rational design of the monomer allows to prepare tailor-made materials. The use of nitrogen-based polydentate building blocks provides specific and versatile functional groups to allow a robust binding site and/or ligand for metal complexes. In this regard, a rigid and planar tris-bidentate ligand-based 5,6,11,12,17,18-hexaazatrinaphthylene (HATN) ligand was employed for the preparation of highly porous and stable Covalent Triazine Frameworks (CTFs). The resulting HATN-based CTF exhibits a remarkably high BET surface area of 1684 m2/g and a total pore volume of 0.79 cm3/g. After post-synthetic metalation with a Cu(OAc)2 complex, it can be utilized as an efficient heterogeneous catalyst for the Henry reaction of aromatic aldehydes and nitromethane under mild reaction conditions. The Cu@HATN-CTF catalyst exhibit an excellent catalytic performance and a higher TON than the conventional Cu-based porous materials. This is probably due to the geometry and the electronic configuration effect, as the paddlewheel structure of the complex is broken upon grafting onto the HATN-CTF.
Polymer supported DMAP: An easily recyclable organocatalyst for highly atom-economical Henry reaction under solvent-free conditions
Das, Diparjun,Pathak, Gunindra,Rokhum, Lalthazuala
, p. 104154 - 104163 (2016)
Polymer supported catalysts are regarded as a borderline class of catalysts, which retains the advantages of homogeneous catalysts while securing the ease of recovery by simple filtration and workup of heterogeneous systems. Additionally, such catalysts are less hygroscopic due to the long polymer backbone. Here we have demonstrated that a catalytic amount of polymer supported DMAP (10 mol%) can lead to excellent conversion of an equimolar mixture of aldehyde and nitroalkane exclusively into β-nitroalcohols via the Henry reaction. Unlike most of the commonly used catalysts, polymer supported DMAP can be recovered by simple filtration and reused several times, thereby reducing the operational cost. High synthetic efficiency, total atom economy, near quantitative yields, mild reaction conditions, operational simplicity, easy recovery and reusability of the catalyst, solvent-free reaction conditions and avoidance of traditional reaction workup make the protocol highly significant from Green and Sustainable Chemistry perspectives.
Merging Asymmetric Henry Reaction with Organocatalytic Cascade Reaction for the Construction of a Chiral Indolizidine Alkaloid Skeleton
Zhou, Yirong,Yang, Qin,Shen, Jian,Chen, Xin,Peng, Yiyuan,Gong, Yuefa
, p. 1446 - 1456 (2015)
A sequential reaction combining the copper-catalyzed asymmetric Henry reaction with the organocatalytic Michael addition-hemiacetalization cascade reaction was developed. The C1-symmetric chiral diamine L1-copper complex was responsible for the first highly enantioselective Henry reaction, while diphenylprolinol silyl ether A acted as effective organocatalyst for the second cascade reaction between chiral β-nitro alcohol and α,β-unsaturated aldehydes. Via rational design and combination of the two independent catalytic systems, good yields and excellent enantioselectivities and diastereoselectivities were achieved for a broad substrate scope under mild reaction conditions. The synthetic utility of this sequential catalytic asymmetric cascade reaction was demonstrated as an alternative and straightforward stereoselective synthesis strategy for chiral indolizidine alkaloid and its analogues.
Ba/ZrO2 nanoparticles as efficient heterogeneous base catalyst for the synthesis of β-nitro alcohols and 2-amino 2-chromenes
Pradhan, Sagnika,Swarnima, Kumari,Mishra
, p. 1119 - 1130 (2016)
Zirconia nanoparticles were synthesized by precipitation, urea hydrolysis, amorphous citrate and combustion synthesis methods. The zirconia surface was subsequently modified by grafting Ba 2+ species. The Ba 2+ modified zirconia (Ba/ZrO 2) materials were characterized using XRD, Fourier analysis, UV-vis-DRS, FESEM and HRTEM techniques. XRD study indicated selective stabilization of the tetragonal phase of zirconia in the presence of Ba 2+ species. Fourier line profile analysis of the XRD peaks revealed that the average crystallite size of the zirconia nanoparticles is in the range of 5-15 nm. The surface area, basicity and barium content of the material depend strongly on the method of synthesis. The Ba/ZrO 2 catalyst prepared by urea hydrolysis method exhibited higher surface area and barium content compared to other samples. The catalytic activity of the Ba/ZrO 2 catalyst was evaluated for synthesis of β-nitro alcohols and 2-amino 2-chromenes. The β-nitro alcohols were synthesized by condensation of aryl aldehydes and nitromethane. Similarly, the 2-amino 2-chromenes were synthesized by condensation of arylaldehydes, α-naphthol and malononitrile. The Ba/ZrO 2 catalyst was found to be highly efficient for synthesis of both classes of compounds providing excellent yield and purity of the products. [Figure not available: see fulltext.]
Application of natural feedstock extract: The Henry reaction
Surneni, Naresh,Barua, Nabin C.,Saikia, Bishwajit
, p. 2814 - 2817 (2016)
For the first time, we have successfully performed the Henry reaction in neat 'Natural Feedstock Extract' at room temperature. Herein, we used two most abundant natural feedstock extracts such as 'Water Extract of Banana' (WEB) and 'Water Extract of Rice Straw Ash' (WERSA). This protocol is highly advantageous owing to the employment of natural feedstock as green reaction media resulting in significant novelty and advancement with respect to green and sustainable chemistry.
Henry reaction catalyzed by copper(I) complexes of a new pyridine-containing macrocyclic ligand
Castano, Brunilde,Pedrazzini, Tommaso,Sisti, Massimo,Gallo, Emma,Ragaini, Fabio,Casati, Nicola,Caselli, Alessandro
, p. 824 - 829 (2011)
The synthesis and characterization of copper(I) complexes of the novel pyridine-containing macrocyclic ligand (PC-L) and their use as catalysts in the Henry reaction are reported. The pyridine-based 12-membered tetraaza macrocyclic (PC-L) ligand 1 can be
Synthesis, structure, and application of self-assembled copper(II) aqua complex by H-bonding for acceleration of the nitroaldol reaction on water
Jammi, Suribabu,Ali, Md Ashif,Sakthivel, Sekarpandi,Rout, Laxmidhar,Punniyamurthy, Tharmalingam
, p. 314 - 320 (2009)
Copper(II) aqua complex 1 has been prepared in a one-pot synthesis. The single crystal X-ray analysis showed that the complex is self-assembled through aqua ligands by H-bond interactions and the copper(II) atoms are pentacoordinated with square pyramidal geometry. Complex 1 has been studied for the acceleration of the nitroalodol reaction on water. It is a clean technological process and the catalyst can be recycled without loss of activity.
Rational design of sterically and electronically easily tunable chiral bisimidazolines and their applications in dual lewis acid/brensted base catalysis for highly enantioselective nitroaldol (Henry) reactions
Ma, Kuoyan,You, Jingsong
, p. 1863 - 1871 (2007)
A new addition to the rational design of sterically and electrically easily tunable chiral bis(imidazoline) ligands from chiral amino alcohols has been developed. Vast structural variation of chiral bis(imidazoline) ligands can be simply achieved by the choice of both the 1,2-amino alcohol and its N-1 R 1 substituent. A small library of chiral bisimidazolines (1a-h) has been constructed. The method has provided an easy and simplified route to a diverse set of air-stable and water-tolerant chiral bis(imidazoline) ligands on 10 g scales. The dual Lewis Acid/Bronsted base catalytic system generated from the (5)-1a/Cu(OTf)2 complex and Et3N was able to catalyze Henry reactions between aldehydes and nitromethane effectively at room temperature, and also to tolerate a wide scope of aldehydes with excellent enantiomeric excesses. Not only aromatic aldehydes but also aliphatic aldehydes afforded the nitroalcohol products, with enantiomeric excesses in the 93-98% range. This dual catalytic system is among the most effective systems so far reported for the asymmetric parent Henry reactions. This work also represents the first members of the class of chiral bisimidazolines to have been demonstrated to achieve excellent enantioselectivities.
