95137-37-4Relevant academic research and scientific papers
Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction
Saravana Ganesan, Nagappan,Suresh, Palaniswamy
, p. 1197 - 1210 (2021/01/07)
Abstract: Simple and easily preparable graphene oxide (GO) is used as a straightforward carbocatalyst for the synthesis of β-amino ketones via a 3-component Mannich reaction under mild condition. The native GO is acting as a carbonaceous solid Br?nsted acid catalyst without any special functionalization, yielding a spectrum of β-amino ketones under metal-free conditions. The present catalytic method offers a benign and simple procedure without any hazardous workup, and chromatographic purification resulted in an excellent yield of β-amino ketones. The catalyst has shown good sustainability up to 6 consecutive catalytic cycles without any significant loss in its activity. The stability of the recovered catalyst is proved by analytical techniques such as FT-IR, PXRD, SEM, and TEM. This mild solid-acid catalyst offers an alternative and sustainable approach to get synthetically essential β-amino ketones under greener conditions. Graphical abstract: [Figure not available: see fulltext.].
Air-stable Organoantimony (III) Perfluoroalkyl(aryl)sulfonate complexes as highly efficient, selective, and recyclable catalysts for C–C and C–N bond-forming reactions
Fan, Qi,Guo, Rui,Li, Ningbo,Ma, Rong,Qiao, Jie,Xu, Li,Xu, Shitang,Xu, Xinhua,Yun, Kemin
, (2021/07/08)
A series of air-stable organoantimony (III) perfluoroalkyl(aryl)sulfonate complexes with an azastibocine framework {t-BuN(CH2C6H4)2SbOSO2C4F9 (2a); [t-BuN(CH2C6/
Ionic liquid-immobilized proline(s) organocatalyst-catalyzed one-pot multi-component Mannich reaction under solvent-free condition
Prabhakara,Maiti, Barnali
, p. 2381 - 2401 (2020/01/31)
A highly efficient clean and simple methodology has been established for the one-pot Mannich reaction using ionic liquid-immobilized proline(s) organocatalyst under solvent-free conditions. The three components comprising substituted acetophenones, substituted aromatic aldehydes and substituted aromatic amines underwent Mannich reactions in the presence of 7?mol% of ionic liquid-immobilized proline(s) organocatalyst to provide β-amino carbonyl compounds in 2–3?h at room temperature with excellent yields. This methodology provides several advantages such as mild reaction conditions, short reaction time, low catalyst loading percentage, multi-component approach, transition metal-free and solvent-free synthesis. The ionic liquid-immobilized proline(s) organocatalyst was recycled and reused five times without a significant loss of its catalytic activity.
Ultrasonic-assisted green synthesis of β-amino carbonyl compounds by copper oxide nanoparticles decorated phosphate functionalized graphene oxide via Mannich reaction
Achary, L. Satish K.,Nayak, Pratap S.,Barik, Bapun,Kumar, Aniket,Dash, Priyabrat
, p. 137 - 147 (2019/09/03)
A facile chemical synthetic route has been demonstrated for the synthesis of copper oxide nanoparticles decorated phosphate functionalized graphene oxide (CuO/PGO). The synthesized nanocatalyst was used as an efficient and active candidate for the synthesis of β-amino carbonyl compounds viaa green synthetic ultrasonic route. The structural properties of the samples were investigated by means of a number of sophisticated techniques like X-ray diffraction (XRD), Fourier-transform Infrared (FTIR) spectroscopy, High Resolution Transmission Electron Microscope (HRTEM), N2 adsorption-desorption measurements, X-ray photoelectron spectroscopy (XPS) analysis, Ammonia temperature programmed desorption analysis (NH3-TPD) and Raman spectroscopy. HRTEM analysis confirmed the presence of spherical CuO nanoparticles distributed uniformly throughout the PGO surface. XPS analysis demonstrated the presence of Cu2+ species and minor reduction of oxygen functional groups on GO. A higher surface area of 162 m2/g for CuO/PGO was found from N2 adsorption-desorption isotherms. Later on, the presence of acidic groups on CuO/PGO that play an essential role in the catalytic activity was examined by NH3-TPD and pyridine adsorbed IR analysis. The total acidity on the surface of synthesized nanocatalyst was found to be of 0.59 mmol g?1 which includes both Lewis as well as Br?nsted acidic sites. A higher product yield of 95% in a shorter period of time of 15 min was achieved which is superior to many reported catalytic systems. A combined strategy involving greener and easier ultrasonic route and use of an efficient acidic graphene oxide-based catalyst resulted in higher catalytic activity and stability with good recyclability.
Hf(OTf)4 as a highly potent catalyst for the synthesis of Mannich bases under solvent-free conditions
Gong, Shan-Shan,Han, Shuai-Bo,Liu, Rong,Peng, Xiao-Chong,Sun, Qi,Wei, Jing-Ying
, (2020/01/28)
Hf(OTf)4 was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)4-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. 1H NMR tracing of the H/D exchange reaction of ketones in MeOH-d4 indicated that Hf(OTf)4 could significantly promote the keto-enol tautomerization, thereby contributing to the acceleration of reaction rate.
An uncommon use of irradiated flavins: Br?nsted acid catalysis
Arakawa, Yukihiro,Mihara, Tomohiro,Fujii, Hiroki,Minagawa, Keiji,Imada, Yasushi
supporting information, p. 5661 - 5664 (2020/06/09)
We present that thioacetalization of aldehydes can be induced by blue light irradiation in the presence of a catalytic amount of riboflavin tetraacetate (RFTA) under aerobic conditions. Several control experiments have suggested that the reaction is more
Titanium tetrachloride incorporated crosslinked polystyrene copolymer as an efficient and recyclable polymeric Lewis acid catalyst for the synthesis of Β-amino carbonyl compounds at room temperature
Rahmatpour, Ali,Eeimen, Reza,Goodarzi, Niloofar
, p. 2915 - 2930 (2019/08/30)
An efficient and eco-friendly procedure for one-pot synthesis of β-amino carbonyl compounds by three-component reaction of aromatic aldehydes, acetophenone, and aromatic amines via a Mannich type reaction using a stable tightly bound complex, titanium tetrachloride incorporated crosslinked polystyrene copolymer (PS/TiCl4), as a water tolerant, recoverable, and reusable polymeric Lewis acid catalyst in ethanol at room temperature is reported. The complex of the polystyrene and TiCl4 provides a shelf-stable acidic, water tolerant material, and it is not easily hydrolyzed by water. Our findings thus show a novel and improved modification of the Mannich type reaction in terms of mild reaction conditions, clean reaction profiles, applicability to various substrates using a simple workup procedure which makes this reaction an interesting alternative to previously applied procedures. The recyclability of the catalyst makes this protocol environmentally benign.
Green synthesis of aminocarbonyl compounds using a nanostructured heterogeneous catalyst under mild reaction conditions
Maleki, Ali,Firouzi-Haji, Razieh
, p. 132 - 135 (2019/07/03)
The synthesis of aminocarbonyl derivatives as biologically active compounds by using polyethylene glycol (PEG-400)-SO3H-coated Fe2O3 is reported. The heterogeneous nanocatalyst was prepared via in-situ co-precipitation met
Tartaric acid-zinc nitrate as an efficient brnsted acid-assisted lewis acid catalyst for the mannich reaction
Dong, Hao Donga,Liu, Qing,Tian, Yuanyu,Qiao, Yingyun
, p. 463 - 466 (2018/10/15)
Tartaric acid-zinc nitrate has been found to be an efficient Brnsted acid-assisted Lewis acid catalytic system for the facile synthesis of β-amino carbonyl compounds through the one-pot Mannich reaction of aldehydes, aromatic amines and ketones in ethanol at room temperature. Remarkable enhancement of reactivity by tartaric acid (Br?nsted acid) was observed in these reactions in the presence of anhydrous zinc nitrate (Lewis acid), due to coordination of the tartaric acid ligand to zinc ions increasing the acidity of the system. This procedure shows some advantages such as mild reaction conditions, short reaction times and high yields.
