27618-25-3Relevant academic research and scientific papers
Green synthesis of CuO nanoparticles using: Lantana camara flower extract and their potential catalytic activity towards the aza-Michael reaction
Chowdhury, Rakesh,Khan, Aslam,Rashid, Md. Harunar
, p. 14374 - 14385 (2020/04/23)
Aza-Michael addition is one of the most exploited reactions in organic chemistry. It is regarded as one of the most popular and efficient methods for the creation of the carbon-nitrogen bond, which is a key feature of many bioactive molecules. Herein, we report the synthesis of CuO nanoparticles by an alkaline hydrolysis process in the presence of the flower extract of Lantana camara, an invasive weed, followed by calcination in air at 400 °C. Microscopic results indicated that the plant extract played an important role in the modulation of the size and shape of the product. In the presence of extract, porous CuO nanostructures are formed. While mostly aggregated rod-shaped CuO nanostructures are formed in the absence of extract. The products are pure and highly crystalline possessing the monoclinic phase. The CuO nanoparticles have been used as a catalyst in the aza-Michael addition reaction in aqueous medium under ultrasound vibration. The product yield is excellent and the catalyst is reusable up to the fifth cycle. The catalyst system can be extended to various substituted substrates with excellent to moderate yields.
Boric acid/glycerol as an efficient catalyst for synthesis of thiomorpholine 1,1-dioxide by double michael addition reaction in water
Halimehjnai, Azim Ziyaei,Hosseyni, Seyedmorteza,Gholami, Hadi,Hashemi, Mohammed M.
, p. 191 - 197,7 (2020/09/02)
Thiomorpholine 1,1-dioxides were prepared with double Michael addition reaction of aromatic amines to divinyl sulfone catalyzed by boric acid/glycerol in water. This catalyst system was also used for the Michael addition reaction of aromatic amines to electron-deficient alkenes. The reaction is simple and green and gives good to excellent yields.
Hydroamination and alcoholysis of acrylonitrile promoted by the pincer complex {κP,κC,κP-2,6- (Ph2PO)2C6H3}Ni(OSO 2CF3)
Salah, Abderrahmen B.,Offenstein, Caroline,Zargarian, Davit
experimental part, p. 5352 - 5364 (2011/12/13)
This report describes the catalytic activity of the pincer-type complex {κP,κC,κP-2,6-(Ph 2PO)2C6H3}Ni(OSO2CF 3) (1) in the anti-Markovnikov addition of aliphatic and aromatic amines and alcohols to acrylonitrile, crotonitrile, and methacrylonitrile. The influence of additives on the catalytic activities was investigated, and it was found that substoichiometric quantities of water promoted the C-N bond forming reactions catalyzed by 1, especially the reactions involving aromatic amines; in comparison, NEt3 had a less dramatic impact. The opposite pattern was observed for the alcoholysis of acrylonitrile promoted by 1: water had no beneficial effect on these reactions, while NEt3 proved to be a potent promoter. Another important difference between these reactions is that hydroamination works better with more nucleophilic amines, whereas the alcoholysis reactions work well with ArOH, CF3CH2OH, and ArCH2OH but not at all with the more nucleophilic aliphatic alcohols methanol, ethanol, and 2-propanol. Both hydroamination and alcoholysis proceed much better with acrylonitrile in comparison to its Me-substituted derivatives crotonitrile and methacrylonitrile. Under optimized conditions, precatalyst 1 promotes conjugate additions to acrylonitrile with catalytic turnover numbers of up to 100 (hydroamination) or higher (alcoholysis). Spectroscopic studies have established that the main Ni-containing species in the hydroamination reactions is a cationic adduct in which the olefinic substrate is bound to the Ni center via its nitrile moiety; this binding activates the double bond toward an outer-sphere nucleophilic attack by the amine (Michael addition). The solid-state structures of the cationic nitrile adducts [{κP, κC,κP-2,6-(Ph2PO)2C 6H3}Ni(NCR)][OSO2CF3] (R = Me (2a), CH2CH2N(H)Ph (2e)), which can be regarded as model complexes for the species involved in the hydroamination catalysis, have been elucidated. Also reported are the solid-state structures of the charge-neutral compound {κP,κC,κP-2,6-(i- Pr2PO)2C6H3}Ni(OSO 2CF3) and an octahedral Ni(II) species resulting from the aerobic/hydrolytic oxidation of 1.
An effective aza-michael addition of aromatic amines to electron-deficient alkenes in alkaline Al2O3
Ai, Xin,Wang, Xin,Liu, Jin-Ming,Ge, Ze-Mei,Cheng, Tie-Ming,Li, Run-Tao
experimental part, p. 5373 - 5377 (2010/08/06)
Aza-Michael addition of aromatic or aliphatic amines with various electron-deficient alkenes was performed using alkaline Al2O 3 as solid media at room temperature afforded the corresponding Michael addition products in good to excellent yields.The alkaline Al 2O3 can be easily recovered and reused.
Functionalized ionic liquid promoted aza-michael addition of aromatic amines
Liu, Xiao-Bing,Lu, Ming,Lu, Ting-Ting,Gu, Guo-Liang
experimental part, p. 1221 - 1226 (2011/10/02)
A functionalized ionic liquid, 3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]) has been used as catalyst for the aza-Michael reactions of aromatic amines with α,β-unsaturated compounds at room temperature to produce β-amino compounds in good yields. The catalyst can be reused for several times without obvious loss of the catalytic activity.
A catalytic method for room-temperature Michael additions using 12-tungstophosphoric acid as a reusable catalyst in water
Chen, Xiang,She, Jin,Shang, Zhicai,Wu, Jun,Zhang, Peizhi
experimental part, p. 3931 - 3936 (2009/05/26)
12-Tungstophosphoric acid (H3PW12O40) has been found to be an efficient and recyclable catalyst in promoting room temperature Michael additions of amines and aryl thiols to α,β- unsaturated esters and acrylonitrile in water to afford the corresponding saturated amines in good to excellent yields. Georg Thieme Verlag Stuttgart.
