29246-34-2Relevant academic research and scientific papers
Multi-functional aromatic amine compound as well as preparation method and application thereof
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, (2021/08/14)
The invention belongs to the technical field of synthesis of aromatic amine compounds, and particularly relates to a multi-functional aromatic amine compound as well as a preparation method and application thereof. The invention provides a multi-functional aromatic amine compound and also provides a preparation method of the multi-functional aromatic amine compound. The amination reaction of aromatic carboxylic acid is catalyzed by DMAP at a relatively low temperature under the condition of no transition metal, and the method can be used for synthesizing a series of multi-functional aromatic amine compounds. The preparation method has not been reported in literature at present. The invention also provides a derivative product of arylamine and a preparation method thereof, and an application of the multi-functional aromatic amine compound in later modification of active molecules. The compound can be used for construction of optical active urea compounds and some important active molecules, and has a development prospect in synthesis of active drugs and natural products.
Silver-Enabled General Radical Difluoromethylation Reaction with TMSCF2H
Yang, Jun,Zhu, Shengqing,Wang, Fang,Qing, Feng-Ling,Chu, Lingling
supporting information, p. 4300 - 4306 (2020/12/25)
A silver-mediated oxidative difluoromethylation of styrenes and vinyl trifluoroborates with TMSCF2H is reported for the first time. This method enables direct and facile access to CF2H-alkenes from abundant alkenes with excellent functional-group compatibility. Moreover, this Ag/TMSCF2H protocol could further enable a series of radical difluoromethylation reactions of a wide array of substrates, offering a generic and complementary platform for the construction of diversified C?CF2H bonds.
Palladium-Catalyzed Carbonylative Four-Component Synthesis of β-Perfluoroalkyl Amides
Geng, Hui-Qing,Wu, Xiao-Feng,Zhang, Youcan
supporting information, p. 17682 - 17687 (2021/10/25)
Transition-metal-catalyzed multicomponent carbonylation is one of the most efficient strategies to construct carbonyl-containing compounds. Herein, a palladium-catalyzed four-component perfluoroalkylation/aminocarbonylation of unactivated alkenes with per
Copper-Catalyzed Electrophilic Amidation of Organotrifluoroborates with Use of N-Methoxyamides
Banjo, Shona,Nakasuji, Eiko,Meguro, Tatsuhiko,Sato, Takaaki,Chida, Noritaka
, p. 7941 - 7947 (2019/05/24)
A copper-catalyzed electrophilic amidation of aryltrifluoroborates with use of N-methoxyamides is reported. The reaction shows high functional group compatibility derived from two distinct features: 1) the high stability of the N-methoxyamides and 2) the nonbasic mild conditions in the presence of LiCl. The developed method can also be applied to the synthesis of enamides, which are widely distributed in natural products. Preliminary mechanistic studies suggest that the initial step is the transmetalation of the aryltrifluoroborate by the assistance of LiCl, and the resulting aryl copper intermediate provides the anilide through non-SN2 oxidative addition to the N-methoxyamide and subsequent reductive elimination.
Metallic magnesium: an efficient catalyst toward N-aryl and N-alkyl substituted amides directly from aliphatic carboxylic acids
Yildirim, Ayhan
, p. 947 - 951 (2015/08/06)
Abstract An efficient and inexpensive procedure for direct conversion of aliphatic carboxylic acids into amides has been developed using anilines or aliphatic amines and Mg(0) as catalyst in toluene. The amides were obtained by single crystallization in moderate to excellent yields with high purity. Graphical Abstract: [Figure not available: see fulltext.]
Selective formation of α,ω-ester amides from the aminocarbonylation of castor oil derived methyl 10-undecenoate and other unsaturated substrates
Jimenez-Rodriguez, Cristina,Nunez-Magro, Angel A.,Seidensticker, Thomas,Eastham, Graham R.,Furst, Marc R. L.,Cole-Hamilton, David J.
, p. 2332 - 2339 (2014/07/22)
The reaction of long chain alkenes with CO and aniline in the presence of palladium complexes of 1,2-bis-(ditertbutylphosphinomethyl)benzene produces amides with high linear selectivity, with much higher rates and catalyst stability when 2-naphthol and sodium or potassium iodide are added. Unsaturated esters including methyl 10-undecenoate from castor oil give α,ω- ester amides, whilst reactions in THF give N-phenylpyrrolidine.
Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively
Nakatsuji, Hidefumi,Morimoto, Mami,Misaki, Tomonori,Tanabe, Yoo
, p. 12071 - 12080 (2008/03/13)
We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.
Synthesis of medium and large cyclic amines in rhodium-catalysed reactions of aminoalkenes with H2/CO1
Bergmann, David J.,Campi, Eva M.,Roy Jackson,Patti, Antonio F.,Saylik, Dilek
, p. 835 - 844 (2007/10/03)
Rhodium-catalysed reactions of N-benzyl- or N-alkyl-aminoalkenes (6) with H2/CO can give cyclic amines (7) (7-13 ring size) in good to excellent yields when BIPHEPHOS is used as a ligand. Hydrogenation of the aminoalkene becomes a competing reaction for the smaller rings but can be overcome by using a H2/CO gas ratio of 1:5. Reactions of 2-alkenyloxybenzylamines (13) gave 9-, 12- and 17-membered rings (14) in 30-40% yield, but dimer formation (16) and/or hydrogenation were competing reactions. Similar reactions of alkenylamides and ortho-alkenylanilines gave only non-cyclized amino aldehydes as products in low isolated yields.
Insect Juvenile Hormone Analogues: Part VII - Synthesis of Long Chain Aromatic Ethers & Nitrogen Analogues
Vig, O. P.,Trehan, I. R.,Kad, G. L.,Dhawan, R. K.,Grewal, M. S.
, p. 688 - 691 (2007/10/02)
Syntheses of various aromatic ethers of undecenyl bromide and thio ethers of undecenyl and undecanyl bromides with 2-benzothiazolethiol are described.The preparation of a few amides and their corresponding amines from undecenoic acid and different aromatic amines and benzyl amine are also reported.The bromo derivatives of a few amides have also been prepared.These compounds have been tested on common Indian red cotton bug for their juvenile hormone activity.
