- Ligand-free copper-catalyzed direct amidation of diaryliodonium salts using nitriles as amidation reagents
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An efficient and practical methodology for the synthesis of N-arylamides has been developed via copper-catalyzed amidation of diaryliodonium salts with nitriles. Various substituted aryl nitriles and aliphatic nitriles could be applied in the reaction, providing a series of N-arylated amides in moderate to good yields. This procedure provides an alternative route for the synthesis of various N-arylamides. A proposed mechanism based on control experiments is also presented.
- Cheng, Hui-cheng,Guo, Penghu,Ji, Hong-bing,Ma, Jiao-li,Zhang, Yang,Zhou, Lichao,Zhou, Xuming
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supporting information
(2021/04/19)
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- Preparation method of N-aryl amide compound
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The invention discloses a preparation method of an N-aryl amide compound, which comprises the following steps: (1) putting diaryliodonium salt and Cu(OAc)2 into a Schlenk tube provided with a magneticstirring rod; (2) sequentially adding DCE, H2O and nitrile by using an injector, sealing the Schlenk tube, and stirring for reaction at 80 DEG C; (3) cooling the obtained solution to room temperature, and performing extraction with EtOAc; and combining organic layers, performing washing with saline water, and performing drying with anhydrous Na2SO4; and (4) removing volatile matters in vacuum, and purifying residues through column chromatography to obtain the N-aryl amide compound. Through a large number of experiments, a substrate with a simple structure is screened, the reaction conditionsare mild, the yield is high, the pollution is small, and the application prospect is wide.
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Paragraph 0102-0106
(2020/07/13)
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- A one pot protocol to convert nitro-arenes into: N-aryl amides
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A two-step one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the methodology was applied to the reaction with γ-butyrolactone, the desired N-aryl butanamide derivative was obtained, featuring a chlorine atom at the γ-position, a functionalized handle that can be used for further synthetic manipulation of the reaction product. Such an intermediate has already been employed as a key advanced precursor of pharmaceutically active compounds.
- Massolo, Elisabetta,Pirola, Margherita,Puglisi, Alessandra,Rossi, Sergio,Benaglia, Maurizio
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p. 4040 - 4044
(2020/02/04)
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- Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature
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The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.
- Mei, Chong,Lu, Wenjun
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p. 4812 - 4823
(2018/04/26)
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- Reductive acylation of nitroarenes to anilides by sodium sulfite in carboxylic acids
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A facile and efficient reductive acylation of aromatic nitro compounds to corresponding anilides using a sodium sulfite-carboxylic acid system for the first time has been reported. The sodium sulfite reagent provides the colorless reductant in combination with stoichiometric amounts of carboxylic acid and enables the formation of anilides from nitroarenes without any additives in good to excellent yields with high purities and simple work-up. Furthermore, this protocol provides a novel and complementary access to some industrially important chemicals in kilogram scale under mild conditions.
- Ghaffarzadeh, Mohammad,Akhavan, Pegah
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supporting information
p. 1417 - 1419
(2016/09/28)
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- Direct hydrogenation of nitroaromatics and one-pot amidation with carboxylic acids over platinum nanowires
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A novel ultrathin platinum nanowire with uniform length and a diameter of 1.5 nm was synthesized by acidic etching of FePt nanowire in methanol. This nanowire was characterized by high-resolution transmission electron microscopy (HRTEM). X-ray diffraction (XRD) data indicated that the main plane is (111). The ability of this nanowire to catalyze the heterogeneous hydrogenation of nitroaromatics to give the corresponding amines has been investigated. The catalyst showed satisfactory activity in various solvents under mild conditions and showed excellent stability. The catalytic performance was also evaluated in the one-pot reduction of nitroaromatics and amidation with carboxylic acids under a hydrogen atmosphere at 100°C. These methods for the hydrogenation of nitroaromatics and the direct amidation of nitroaromatics with carboxylic acids are simple, economical, and environmentally benign, and have practical advantages for the synthesis of amines and amides without the production of toxic byproducts.
- Li, Min,Hu, Lei,Cao, Xueqin,Hong, Haiyan,Lu, Jianmei,Gu, Hongwei
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supporting information; experimental part
p. 2763 - 2768
(2011/04/12)
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- Infrared spectra of N-aryl substituted amides 2/4-XC6H 4NHCOR (R = H, CH3-iXi, C6H 5 or C6H5Cl; X = H, Cl or CH3 and i = 0, 1, 2 or 3)
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Several N-(aryl)-substituted amides of the general formula, 2/4-XC 6H4NHCOR (where X = H, Cl or CH3 and R = H, CH3, CH2CH3, CH(CH3)2, C(CH3)3, C6H5 or C6H 5Cl) are prepared, characterised and their infrared spectra measured in the solid state and analysed. Generally chloro substitution in the side chain increases the C=O absorptions, while that of methyl groups lower the wave numbers. Amides with trimethyl substituted side chains absorb at higher wavenumbers. But the N-H and C-N stretching vibrations do not show particular trends on side chain substitution. This may be due to the fact that the spectra were recorded in the solid state and the compounds may crystallise in different forms in the solid state. The intercorrelations of C=O and N-H absorption frequencies of all the amides have been made. The correlations are reasonably linear with some exceptions for the reasons stated above.
- Gowda, B. Thimme,Jyothi,Jayalakshmi,Damodara
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p. 564 - 568
(2007/10/03)
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- Electrochemical determination of the pKa of weak acids in N,N-dimethylformamide
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The electroreduction of NH-protic α-bromo amides in DMF generates an enolate-type base which undergoes a fast proton transfer from the parent compound (self-protonation), affording the corresponding reduced amide together with the conjugate base of the br
- Maran, Flavio,Celadon, Dino,Severin, Maria Gabriella,Vianello, Elio
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p. 9320 - 9329
(2007/10/02)
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- ELECTRO-CARBOXYLATION OF 2-BROMOISOBUTYRAMIDES. A USEFUL SYNTHETIC WAY TO ESTER-AMIDES OF 2,2-DIMETHYLMALONIC ACID
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The electroreduction of protic 2-bromoisobutyramides was studied in acetonitrile in the presence of carbon dioxide by means of cyclic voltammetry and controlled-potential electrolysis.The electrogeneration of the α-carbanion is followed by a fast and quan
- Maran, Flavio,Fabrizio, Monica,D'Angeli, Ferruccio,Vianello, Elio
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p. 2351 - 2358
(2007/10/02)
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