1485-72-9Relevant academic research and scientific papers
Rhodium-catalyzed arylation and alkenylation of imines with organostannanes
Oi, Shuichi,Moro, Mitsutoshi,Fukuhara, Hiroe,Kawanishi, Takanori,Inoue, Yoshio
, p. 9259 - 9262 (1999)
A rhodium complex catalyzed the addition of aryl- and alkenyl-stannanes to activated aldimines under mild and neutral conditions, affording the corresponding amines in good yields.
A mild and efficient method for formation of C-N bond from benzyl alcohols and sulfonamide, carboxamide, 4-nitroanline and azide catalysed by SnCl 4
Li, Lingjun,Zhu, Anlian,Yao, Huiwen,Wei, Yujing,Yang, Di,Li, Jianping,Zhang, Guisheng
, p. 511 - 513 (2010)
A mild and efficient method for the formation of C-N bonds is reported with SnCl4 as an inexpensive catalyst. With 10 mol% of SnCl4, the direct substitution reaction of secondary benzyl alcohols with a sulfonamide, a carboxamide, 4-nitroaniline and an azide proceeds well in good to excellent yields at room temperature.
Method for synthesizing amide compound by taking nitrile and diaryl methane as raw materials
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Paragraph 0030-0040, (2022/01/20)
The invention discloses a method for synthesizing an amide compound by taking nitrile and diaryl methane as raw materials, the method comprises the following steps: taking diaryl methane as a reaction raw material, nitrile as a raw material and a solvent, 2, 3-dichloro-5, 6-dinitrile group-1, 4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) as catalysts, acid as an auxiliary agent and oxygen as an oxidizing agent, reacting under the conditions of normal temperature, normal pressure and blue light irradiation, and after the reaction is finished, carrying out separation treatment to obtain the amide compound. According to the method, the problem of metal residues in the product can be solved, oxygen is used as a terminal oxidizing agent, the method is environmentally friendly, and energy can be saved.
An expedient, efficient and solvent-free synthesis of T3P-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation
Cheruku, Srinivas,Manikyanally, Kumara N.,Mantelingu, Kempegowda,Nagarakere, Sandhya C.,Narayana, Yatheesh,Rangappa, Kanchugarakoppal S.,Sunilkumar, Makanahalli P.
, p. 4421 - 4426 (2022/03/14)
An expedient, efficient, economical, environmentally benign, and solvent free amidation protocol of benzhydrols with less reactive nitrogen nucleophiles assisted by propylphosphonic anhydride (T3P) under microwave irradiation has been developed. The methodology has been deployed for a wide range of heterocycles and electron-withdrawing & electron-donating groups. The protocol resulted in good to excellent yields under the given conditions (26 examples, 68-93% yield).
Dehydrogenative amide synthesis from alcohols and amines utilizing N-heterocyclic carbene-based ruthenium complexes as efficient catalysts: The influence of catalyst loadings, ancillary and added ligands
Wang, Wan-Qiang,Wang, Zhi-Qin,Sang, Wei,Zhang, Rui,Cheng, Hua,Chen, Cheng,Peng, Da-Yong
, (2021/01/05)
The metal-catalyzed dehydrogenative coupling of alcohols and amines to access amides has been recognized as an atom-economic and environmental-friendly process. Apart from the formation of the amide products, three other kinds of compounds (esters, imines and amines) may also be produced. Therefore, it is of vital importance to investigate product distribution in this transformation. Herein, N-heterocyclic carbene-based Ru (NHC/Ru) complexes [Ru-1]-[Ru-5] with different ancillary ligands were prepared and characterized. Based on these complexes, we selected condition A (without an added NHC precursor) and condition B (with an added NHC precursor) to comprehensively explore the selectivity and yield of the desired amides. After careful evaluation of various parameters, the Ru loadings, added NHC precursors and the electronic/steric properties of ancillary NHC ligands were found to have considerable influence on this catalytic process.
Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions
Joseph, Devaneyan,Lee, Sunwoo,Park, Myeong Seong
supporting information, p. 6227 - 6232 (2021/07/28)
N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.
Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones
Tang, Jing-Jing,Yu, Xiaoqiang,Wang, Yi,Yamamoto, Yoshinori,Bao, Ming
, p. 16426 - 16435 (2021/05/13)
Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.
Preparation method of photocatalytic N-alkylamide compound
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Paragraph 0049-0052, (2021/04/17)
The invention belongs to the technical field of organic synthesis, and provides a preparation method of an N-alkylamide compound. According to the method, a dioxazolone compound and an alkane derivative are used as raw materials, a manganese catalyst and an additive react for 12-24 hours in an organic solvent under a mild condition under photocatalysis, and the product is converted into an N-alkylamide compound. The method has the beneficial effects that the raw materials are cheap and easy to obtain, the conditions are mild, the method is environment-friendly, the possibility of industrialization is realized, and the yield of the N-alkylamide compound is high; the N-alkylamide compound can be further functionalized to obtain various compounds, and is applied to development and research of natural products, functional materials and fine chemicals.
Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis
Chen, Dong-Huang,Sun, Wei-Ting,Zhu, Cheng-Jie,Lu, Guang-Sheng,Wu, Dong-Ping,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 8827 - 8831 (2021/03/16)
The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.
Chemoselective formation of C–N bond in wet acetonitrile using amberlyst-15(H) as a recyclable catalyst
Nandy, Sneha,Das, Asit Kumar,Bhar, Sanjay
supporting information, p. 3326 - 3336 (2020/08/13)
An economically efficient and environmentally benign protocol for the chemoselective one-pot synthesis of diversely N-substituted amides has been developed in good yield through the reaction of benzylic secondary alcohols as well as aliphatic tertiary alcohols and alkyl/aryl nitriles. Commercially available Amberlyst-15(H) has been utilized at 80 °C as an air-stable and reusable heterogeneous inexpensive solid acid catalyst without any anhydrous and inert environment. The attractive features of the present synthetic protocol are mild reaction conditions, short reaction time, excellent chemoselectivity, high atom economy and tolerance of various sensitive moieties.
