2759-55-9Relevant articles and documents
CATALYST FOR CONVERTING ESTER TO AMIDE USING HYDROXYL GROUP AS ORIENTATION GROUP
-
Paragraph 0059-0061, (2021/03/13)
Provided is a method for amidating a hydroxy ester compound at a high chemical selectivity. The amidation reaction method for a hydroxy ester compound comprises, in the presence of a catalyst containing a compound of a transition metal of the group 4 or group 5 in the periodic table, reacting at least one kind of hydroxy ester compound selected from the group consisting of an α-hydroxy ester compound, a β-hydroxy ester compound, a γ-hydroxy ester compound and a δ-hydroxy ester compound with an amino compound so as to amidate an ester group having a hydroxyl group at the α-, β-, γ- or δ-position of the hydroxy ester compound.
Copper-catalyzed Goldberg-type C-N coupling in deep eutectic solvents (DESs) and water under aerobic conditions
Cicco, Luciana,Hernández-Fernández, Jose A.,Salomone, Antonio,Vitale, Paola,Ramos-Martín, Marina,González-Sabín, Javier,Presa Soto, Alejandro,Perna, Filippo M.,Capriati, Vito,García-álvarez, Joaquín
supporting information, p. 1773 - 1779 (2021/03/14)
An efficient and selectiveN-functionalization of amides is first reportedviaa CuI-catalyzed Goldberg-type C-N coupling reaction between aryl iodides and primary/secondary amides run either in Deep Eutectic Solvents (DESs) or water as sustainable reaction media, under mild and bench-type reaction conditions (absence of protecting atmosphere). Higher activities were observed in an aqueous medium, though the employment of DESs expanded and improved the scope of the reaction to include also aliphatic amides. Additional valuable features of the reported protocol include: (i) the possibility to scale up the reaction without any erosion of the yield/reaction time; (ii) the recyclability of both the catalyst and the eutectic solvent up to 4 consecutive runs; and (iii) the feasibility of the proposed catalytic system for the synthesis of biologically active molecules.
Iodine and Br?nsted acid catalyzed C–C bond cleavage of 1,3-diketones for the acylation of amines
Zhou, Xiao-Yu,Chen, Xia,Yang, Dan
supporting information, p. 177 - 184 (2019/11/26)
A metal-free N-acylation method of anilines with 1,3-diketones has been developed, by using iodine and p-toluene sulfonic acid as the co-catalysts. The reaction can proceed in 1,4-dioxane at elevated temperature to produce the corresponding amides with 48–89% yields. Further, the gram-scale experiment was carried out under the standard conditions and the possible mechanism was proposed.
SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
Zhang, Guofu,Zhao, Yiyong,Xuan, Lidi,Ding, Chengrong
supporting information, p. 4911 - 4915 (2019/07/31)
A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.
Cu-Mediated Synthesis of Indolines and Dihydroisoquinolinones through Arylperfluoroalkylation of Unactivated Alkenes
Li, Dandan,Wang, Yan,Jia, Zhenzhen,Ou, Zhaocheng,Dong, Yongrui,Lv, Cunjie,Fu, Guangbin,Liang, Deqiang
, p. 4797 - 4804 (2019/08/12)
The copper-mediated fluroalkylation/cyclization of N-allyl anilines has been described using fluoroalkyl iodides as fluoroalkylation reagents for the first time. The reaction provides an efficient and direct access to 3-fluoroalkyl indolines in moderate to good yields with unactivated double bonds as the radical acceptor. This protocol combines a simple experimental procedure with low-costing fluoroalkylated sources and excellent functional group tolerance.
Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent
Zhang, Xinglu,Liu, Zhiqiang,Gao, Yu,Li, Feng,Tian, Yaming,Li, Chunju,Jia, Xueshun,Li, Jian
supporting information, p. 272 - 277 (2017/11/13)
A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N-arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C?C and C?O bond-forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. (Figure presented.).
Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
Li, Ningbo,Wang, Lingxiao,Zhang, Liting,Zhao, Wenjie,Qiao, Jie,Xu, Xinhua,Liang, Zhiwu
, p. 3532 - 3538 (2018/08/01)
Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.
Preparation method of N-aryl amide compounds
-
Paragraph 0032-0034, (2018/12/13)
The invention belongs to the technical field of synthesis of compounds, and in particular relates to a preparation method of N-aryl amide compounds. The method comprises the following steps: dissolving amide, a copper catalyst and alkali in an organic solvent, and adding a halogenated aromatic hydrocarbon; then, irradiating with ultraviolet light for carrying out a reaction for 12-24h under nitrogen protection; after the reaction is completed, concentrating reaction liquid by using a rotary evaporator; separately and purifying by means of column chromatography silica gel to obtain the N-aryl amide. The method provided by the invention replaces heating with illumination, does not need to add a ligand, is simple in process, mild in conditions and lower in economic cost, and has higher functional group compatibility and universality.
Ni-Catalyzed cross-coupling of aryl thioethers with alkyl Grignard reagents via C-S bond cleavage
Zhu, Dan,Shi, Lei
supporting information, p. 9313 - 9316 (2018/08/29)
A Ni-catalyzed cross-coupling of aryl thioethers with alkyl Grignard reagents, accompanied by the cleavage of the C(aryl)-SMe bond, has been presented. This method is distinguished by its mild conditions and moderate functional group tolerance, such as hydroxyl, halogen, and heterocycles, which should provide a straightforward access to the modification of sulfur-containing molecules.
Carbon Tetrabromide/Triphenylphosphine-Activated Beckmann Rearrangement of Ketoximes for Synthesis of Amides
Gao, Peng,Bai, Zijing
supporting information, p. 1673 - 1677 (2017/10/05)
An efficient Beckmann rearrangement of ketoximes was developed using carbon tetrabromide/triphenylphosphine as an organocatalyst without addition of any acids or metals. The reaction showed good functional group tolerance and gave various amides in moderate to good yields.
