115348-15-7Relevant articles and documents
Preparation method of aryl acetamide compound
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Paragraph 0034-0040, (2020/12/08)
The invention discloses a preparation method of an aryl acetamide compound. The method comprises the following steps: adding a palladium catalyst, a ligand, benzyl formate, tertiary amine and trifluoroacetic anhydride into an organic solvent, performing reacting at 130 DEG C for 24 hours, and after the reaction is completed, carrying out after-treatment to obtain the aryl acetamide compound. The preparation method is easy to operate, the after-treatment is simple and convenient, reaction initial raw materials are cheap and easily available, benzyl formate is taken as both a carbon monoxide source and a reactant, tertiary amine is taken as an amine source, substrate designability is high, substrate functional group tolerance range is wide, and reaction efficiency is high. What is noteworthyis that C-N bonds of the tertiary amine are broken in the reaction, no extra oxidizing agent is needed, various aryl acetamide compounds can be synthesized according to actual needs, and practicability is high.
Direct defluorinative amidation-hydrolysis reaction of gem-difluoroalkenes with N,N-dimethylformamide, and primary and secondary amines
Wang, Biyun,Zhao, Xianghu,Liu, Qingyun,Cao, Song
, p. 8546 - 8552 (2018/12/01)
A novel and efficient method for the synthesis of arylacetamides by the reactions of gem-difluoroalkenes with N,N-dialkylformamides, and primary and secondary amines with the assistance of KOtBu and water was developed.
P450-catalyzed asymmetric cyclopropanation of electron-deficient olefins under aerobic conditions
Renata, Hans,Wang, Z. Jane,Kitto, Rebekah Z.,Arnold, Frances H.
, p. 3640 - 3643 (2015/02/05)
A variant of P450 from Bacillus megaterium five mutations away from wild type is a highly active catalyst for cyclopropanation of a variety of acrylamide and acrylate olefins with ethyl diazoacetate (EDA). The very high rate of reaction enabled by histidine ligation allowed the reaction to be conducted under aerobic conditions. The promiscuity of this catalyst for a variety of substrates containing amides has enabled synthesis of a small library of precursors to levomilnacipran derivatives. This journal is
Direct amidation of carboxylic acids with tertiary amines: Amide formation over copper catalysts through C-N bond cleavage
Xiong, Biquan,Zhu, Longzhi,Feng, Xiaofeng,Lei, Jian,Chen, Tieqiao,Zhou, Yongbo,Han, Li-Biao,Au, Chak-Tong,Yin, Shuang-Feng
supporting information, p. 4244 - 4247 (2014/07/21)
A copper-catalyzed system for the amidation of carboxylic acids with tert-amines through C-N bond cleavage was developed. This protocol is practical and represents a simple way to produce functionalized amides from basic starting materials in moderate to good yields. A plausible mechanism is proposed for the reaction. Copyright
Ketene reactions with tertiary amines
Allen, Annette D.,Andraos, John,Tidwell, Thomas T.,Vukovic, Sinisa
, p. 679 - 685 (2014/04/03)
Tertiary amines react rapidly and reversibly with arylketenes in acetonitrile forming observable zwitterions, and these undergo amine catalyzed dealkylation forming N,N-disubstituted amides. Reactions of N- methyldialkylamines show a strong preference for methyl group loss by displacement, as predicted by computational studies. Loss of ethyl groups in reactions with triethylamine also occur by displacement, but preferential loss of isopropyl groups in the phenylketene reaction with diisopropylethylamine evidently involves elimination. Quinuclidine rapidly forms long-lived zwitterions with arylketenes, providing a model for catalysis by cinchona and related alkaloids in stereoselective additions to ketenes.
A general and practical palladium-catalyzed direct a-arylation of amides with aryl halides
Zheng, Bing,Jia, Tiezheng,Walsh, Patrick J.
supporting information, p. 165 - 178 (2014/03/21)
An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indolebased phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pK a up to 35) were reversibly depotonated by lithium tert-butoxide (LiO-t-Bu), sodium tert-butoxide (NaO-t-Bu) or sodium bis(trimethylsilyl)amide [NaN(SiMe3)2].
Pd(ii)-catalyzed decarboxylative acylation of phenylacetamides with α-oxocarboxylic acids via C-H bond activation
Park, Jihye,Kim, Minyoung,Sharma, Satyasheel,Park, Eonjeong,Kim, Aejin,Lee, Sang Hwi,Kwak, Jong Hwan,Jung, Young Hoon,Kim, In Su
supporting information, p. 1654 - 1656 (2013/03/14)
A palladium-catalyzed decarboxylative acylation of phenylacetamides with α-oxocarboxylic acids via C-H bond activation is described. This protocol provides efficient access to a range of ortho-acyl phenylacetamides, which can be easily converted to 3-isochromanone derivatives. The Royal Society of Chemistry 2013.
Amination of phenylketenes. Substituent effect on amine-catalyzed tautomerization of amide enol
Badal, Md. Mizanur Rahman,Zhang, Min,Kobayashi, Shinjiro,Mishima, Masaaki
, p. 1071 - 1076 (2014/01/06)
The transient intermediates with infrared bands at 1676-1680 cm -1 observed for reaction of substituted phenylketenes with diethylamine in acetonitrile were suggested to be the amide enols rather than the zwitterions on the basis of the theoretical calculations. A single broad band at 1674 cm-1 observed for reaction with the primary amines was attributed to overlap of two bands of the intermediate (amide enol) and the final product (amide). The substituent effect for the second-order rate constants of diethylamine-catalyzed tautomerization of the amide enol intermediates to give the amides was analyzed successfully by the Yukawa-Tsuno equation, giving a ρ value of 0.63 and an r- value of 1.31. The r- value larger than unity for pKa of phenols indicates that the negative charge formed at an oxygen atom of the amide enol at the transition state is significantly delocalized into the aromatic π-system through the ethenyl group. This r- value was considered to reflect an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ value attributes to the cyclic transition structure where the negative charge disperses in a six-member ring. Copyright 2013 John Wiley & Sons, Ltd. The substituent effect for the reaction of the amide enol intermediate generated from phenylketene with diethylamine has been analyzed. The large r- of 1.31 was attributed to an intrinsic property of β-phenylenolate skeleton. A remarkably small ρ of 0.63 suggested the cyclic transition structure. Copyright
Palladium-catalyzed direct intermolecular α-arylation of amides with aryl chlorides
Zheng, Bing,Jia, Tiezheng,Walsh, Patrick J.
supporting information, p. 4190 - 4193 (2013/09/12)
An efficient catalytic system for the direct intermolecular α-arylation of acetamide derivatives with aryl chlorides is presented. Chemoselectivities up to 10:1 in the mono-and diarylation of acetamides were achieved by careful selection of bases, solvent
Practical synthesis of amides from alkynyl bromides, amines, and water
Chen, Zheng-Wang,Jiang, Huan-Feng,Pan, Xiao-Yan,He, Zai-Jun
experimental part, p. 5920 - 5927 (2011/09/19)
A general and efficient method for the synthesis of a wide range of amides is described here. The reactions were conducted under convenient conditions and provided secondary and tertiary amides in moderate to excellent yields. A variety of amines and substituted alkynyl bromides were used to investigate the scope of the reactions.
