7472-54-0Relevant academic research and scientific papers
Nickel-Catalyzed Cross-Electrophile Coupling between C(sp2)-F and C(sp2)-Cl Bonds by the Reaction of ortho-Fluoro-Aromatic Amides with Aryl Chlorides
Nohira, Itsuki,Chatani, Naoto
, p. 4644 - 4649 (2021)
Ni-catalyzed cross-electrophile coupling between C(sp2)-F bonds in ortho-fluoro-substituted aromatic amides and C(sp2)-Cl bonds in aryl chlorides in the presence of Zn as a reductant and LiOtBu as a base, and LiCl and ZnCl2 as additives is reported. The reaction displayed excellent functional group tolerance and a broad substrate scope. The reaction was also applicable to cross-electrophile coupling between C(sp2)-F and C(sp2)-O bonds in an aryl tosylate and a triflate derivative.
In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C-N Bond Formation
Steinsoultz, Philippe,Bailly, Aurélien,Wagner, Patrick,Oliva, Estefania,Schmitt, Martine,Grimaud, Laurence,Bihel, Frédéric
, p. 560 - 567 (2022/01/03)
We report an efficient Buchwald-Hartwig cross-coupling reaction in alcoholic solvent, in which a low catalyst loading showed excellent performance for coupling aryl halides (I, Br, and Cl) with a broad set of amines, amides, ureas, and carbamates under mild conditions. Mechanistically speaking, in a protic and polar medium, extremely bulky biarylphosphine ligands interact with the dimeric precatalyst [Pd(π-(R)-allyl)Cl]2 to form the corresponding cationic complexes [Pd(π-(R)-allyl)(L)]Cl in situ and spontaneously. The resulting precatalyst further evolves under basic conditions into the corresponding L-Pd(0) catalyst, which is commonly employed for cross-coupling reactions. This mechanistic study highlights the prominent role of alcoholic solvents for the formation of the active catalyst.
Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow
Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan
supporting information, (2022/01/06)
Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i
Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
, p. 58 - 63 (2021/12/27)
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
NaOTs-promoted transition metal-free C-N bond cleavage to form C-X (X = N, O, S) bonds
Chen, Wei,Liu, Sicheng,Liu, Tingting,Majeed, Irfan,Ye, Xiaojing,Zeng, Zhuo,Zhang, Yuqi,Zhu, Yulin
supporting information, p. 8566 - 8571 (2021/10/20)
Multifunctional transformation of amide C-N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.
Chromium-catalyzed ligand-free amidation of esters with anilines
Chen, Changpeng,Ling, Liang,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 762 - 766 (2021/04/14)
Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.
Direct Amidation of Esters by Ball Milling**
Barreteau, Fabien,Battilocchio, Claudio,Browne, Duncan L.,Godineau, Edouard,Leitch, Jamie A.,Nicholson, William I.,Payne, Riley,Priestley, Ian
supporting information, p. 21868 - 21874 (2021/09/02)
The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.
Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
supporting information, (2020/12/21)
A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
Method for synthesizing amide derivative under catalysis of vanadium
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Paragraph 0013-0015; 0052-0054, (2021/02/10)
The invention discloses a method for synthesizing an amide derivative under the catalysis of vanadium, which comprises the following step of: by using a nitro aromatic compound and an ester compound as raw materials, a vanadium compound as a catalyst and magnesium chips as a reducing agent, carrying out amidation reaction in an organic solvent to obtain the amide derivative. The method has the advantages that (1) the nitro aromatic compound which is good in stability, low in price and easy to obtain is used as a nitrogen source; (2) the used catalyst is cheap, easy to obtain and low in toxicity; and (3) the method has good substrate applicability, and is suitable for aromatic nitro compounds, fatty esters and aryl esters containing different substituents.
Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution
Wang, Jin,Hou, Huiqing,Hu, Yongzhi,Lin, Jin,Wu, Min,Zheng, Zhiqiang,Xu, Xiuzhi
supporting information, (2021/02/09)
A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.
