82125-93-7Relevant academic research and scientific papers
TBN-Catalyzed Dehydrative N-Alkylation of Anilines with 4-Hydroxybutan-2-one
Cheng, Wenchen,Deng, Shue,Jiang, Liya,Ren, Lanhui,Wang, Zicheng,Zhang, Jian,Song, Weiguo
supporting information, p. 7372 - 7377 (2019/11/28)
Until now, the substitution of alcohols by N-nucleophiles via TBN-catalyzed dehydrogenation was not known. Herein, we reported a TBN catalyzed dehydrative N-alkylation of anilines with 4-hydroxybutan-2-one in the presence of TEMPO, which was different from the TEMPO/TBN catalyzed oxidation reactions. A range of anilines reacted successfully with 4-hydroxybutan-2-one to generate the N-monoalkylation products in good yields. Mechanistic studies revealed that this reaction most possibly proceeded through aza-Michael addition. Water was the only by-product, making it more environmentally friendly. The gram-scale reactions verified the synthetic practicality of this protocol.
Method for catalyzing N-alkylation reaction by TEMPO and TBN
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Paragraph 0054; 0055, (2019/11/20)
The invention discloses a method for catalyzing N-alkylation reaction of aniline and 4-hydroxy-2-butanone by TEMPO and TBN. 4-hydroxy-2-butanone and different anilines are used as the reaction substrate, TEMPO (2,2,6,6-tetramethylpiperidine oxide) is used as catalyst, TBN (tert-butyl nitrite) is used as cocatalyst, dimethyl sulfoxide or N,N-dimethylformamide or toluene is used as solvent, N-alkylation product is obtained in nitrogen atmosphere at room temperature, no other by-products are detected. The preparation method of the invention uses TEMPO and TBN to catalyze aniline compounds and 4-hydroxy-2-butanone to perform N-alkylation reaction.
Palladium-catalyzed oxidative amination of homoallylic alcohols: Sequentially installing carbonyl and amino groups along an alkyl chain
Ouyang, Lu,Huang, Jiuzhong,Li, Jianxiao,Qi, Chaorong,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 10422 - 10425 (2017/09/25)
A novel Pd-catalyzed intermolecular cascade oxidative amination of homoallylic alcohols to yield β-amino ketones has been developed by using TBHP as the terminal oxidant. The synthetic utility of the reaction can be performed by installing the carbonyl an
Palladium-Catalyzed 6-endo-Selective Oxycyclization-Alkene Addition Cascades of ortho-Alkynylarylcarboxamides and α,β-Unsaturated Carbonyl Compounds
Madich, Youssef,álvarez, Rosana,Aurrecoechea, José M.
, p. 6298 - 6305 (2015/10/06)
Regio- and chemoselective palladium-catalyzed cyclization-coupling cascade reactions between ortho-alkynylarylcarboxamides and methyl vinyl ketone or acrylaldehyde are described. An initial 6-endo-oxypalladation of the triple bond is followed by a C-C cou
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.
Amphiphilic methyleneamino synthon through organic dye catalyzed- decarboxylative aminoalkylation
Chen, Li,Chao, Chin Sheng,Pan, Yuanhang,Dong, Sheng,Teo, Yew Chin,Wang, Jian,Tan, Choon-Hong
supporting information, p. 5922 - 5925 (2013/09/12)
The utilization of a photo-induced synthon generated from N-phenyl glycine by an organic dye and visible light irradiation is disclosed. The intermediate could be coupled with either a radical or a nucleophile in a simple operation to afford several natural product-like compounds.
Anodic generation of a zirconium catalyst for Ferrier rearrangement and hetero Michael addition
Stevanovic, Dragana,Pejovic, Anka,Damljanovic, Ivan,Vukic evic, Rastko D.,VukiC evic, Mirjana,Bogdanovic, Goran A.
, p. 6257 - 6260,4 (2012/12/11)
An efficient catalyst for Ferrier rearrangement and hetero-Michael addition was successfully generated from a sacrificial zirconium anode into media containing reactants for these reactions. Thus, the catalyst generated, successfully promoted the allylic
Green, efficient and practical Michael addition of arylamines to α,β-unsaturated ketones
Jiang, Ran,Li, Dan-Hua,Jiang, Jing,Xu, Xiao-Ping,Chen, Tao,Ji, Shun-Jun
supporting information; experimental part, p. 3631 - 3637 (2011/06/21)
The aza-Michael addition of aromatic amines to α,β-unsaturated ketones was carried out effectively at room temperature in good to excellent yields without any catalyst or solvent. It was significant that part of adducts could be collected in almost quanti
Lithium tetrafluoroborate catalyzed highly efficient inter- and intramolecular aza-Michael addition with aromatic amines
Lad,Kulkarni,Desai,Wadgaonkar
experimental part, p. 1059 - 1064 (2012/03/11)
Lithium tetrafluoroborate has been demonstrated for the first time to be an efficient catalyst in intermolecular aza-Michael addition aromatic amines to electron deficient alkenes. Suitability of the same catalyst in intramolecular aza-Michael addition leading 2-aryl-2,3-dihydroquinolin-4(1H) ones has also been described.
"On-water" conjugate additions of anilines
Phippen, Christopher B. W.,Beattie, James K.,McErlean, Christopher S. P.
supporting information; experimental part, p. 8234 - 8236 (2010/12/20)
The conjugate addition of anilines onto unsaturated ketones, esters and N-acylpyrroles was investigated. Based on a recently proposed explanation for the phenomenon of on-water catalysis, operationally simple and mild reaction conditions for effecting these addition reactions have been developed. The success of these additions provides further support for the acid-catalysed nature of on-water chemistry.
