367-97-5Relevant academic research and scientific papers
Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids
Tang, Jing-Jing,Yu, Xiaoqiang,Yamamoto, Yoshinori,Bao, Ming
, p. 13955 - 13961 (2021/11/20)
A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.
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.
Development of a 1,2,4-Triazole-Based Lead Tankyrase Inhibitor: Part II
Aertssen, Sjoerd,Amundsen-Isaksen, Enya,Brinch, Shoshy Alam,Damen, Eddy,Galera-Prat, Albert,Krauss, Stefan,Leenders, Ruben G. G.,Murthy, Sudarshan,Nieczypor, Piotr,Smits, Johannes N.,Sowa, Sven T.,Waaler, Jo,Wegert, Anita,Lehti?, Lari,Nazaré, Marc
, p. 17936 - 17949 (2021/12/17)
Tankyrase 1 and 2 (TNKS1/2) catalyze post-translational modification by poly-ADP-ribosylation of a plethora of target proteins. In this function, TNKS1/2 also impact the WNT/β-catenin and Hippo signaling pathways that are involved in numerous human diseas
Para -Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway
Viveki, Amol B.,Garad, Dnyaneshwar N.,Gonnade, Rajesh G.,Mhaske, Santosh B.
supporting information, p. 1565 - 1568 (2020/02/13)
Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp2)-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.
Palladium-Catalyzed Amide Synthesis via Aminocarbonylation of Arylboronic Acids with Nitroarenes
Peng, Jin-Bao,Li, Da,Geng, Hui-Qing,Wu, Xiao-Feng
supporting information, p. 4878 - 4881 (2019/06/17)
A palladium-catalyzed aminocarbonylation of aryl boronic acids with nitroarenes for the synthesis of amides has been developed. A wide range of substrates were well-tolerated and gave the corresponding amides in moderate to good yields. No external oxidant or reductant was needed in this procedure. This procedure provides a redox-economical process for the synthesis of amides.
Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
Xu, Ze-Ming,Li, Hong-Xi,Young, David James,Zhu, Da-Liang,Li, Hai-Yan,Lang, Jian-Ping
supporting information, p. 237 - 241 (2019/01/10)
Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.
Solvent- and transition metal-free amide synthesis from phenyl esters and aryl amines
Rzhevskiy, Sergey A.,Ageshina, Alexandra A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
, p. 1536 - 1540 (2019/01/24)
A general, economical, and environmentally friendly method of amide synthesis from phenyl esters and aryl amines was developed. This new method has significant advantages compared to previously reported palladium-catalyzed approaches. The reaction is performed transition metal- and solvent-free, using a cheap and environmentally benign base, NaH. This approach enabled us to obtain target amides in high yields with high atom economy.
Method for synthesizing amide compound through photocatalysis in water phase
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Paragraph 0061, (2019/10/01)
The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.
Amide-assisted radical strategy: Metal-free direct fluorination of arenes in aqueous media
Liang, Deqiang,Li, Yanni,Gao, Shulin,Li, Renlun,Li, Xiangguang,Wang, Baoling,Yang, Hai
supporting information, p. 3344 - 3349 (2017/07/28)
A metal- and initiator-free direct fluorination of arenes with the assistance of an amide group is developed. This reaction proceeded under simple aqueous conditions with good functional group tolerance and ortho-para selectivity, and is highly practical because it could be readily scaled up to a multigram-scale. At this stage, an exclusive mechanism could not be proposed, and several possibilities have been discussed. The possibility of the amide-assisted radical chain mechanism has been supported by experimental and computational investigations as well as a seminal work.
Efficient synthesis of amides and esters from alcohols under aerobic ambient conditions catalyzed by a Au/mesoporous Al2O3 nanocatalyst
Chng, Leng Leng,Yang, Jinhua,Ying, Jackie Y.
, p. 1916 - 1925 (2015/06/16)
An efficient heterogeneous Au/mesoporous alumina nanocatalyst has been successfully developed for the synthesis of amides and esters from simple building blocks of readily available alcohols and amines. The processes were simple and were performed at room temperature and atmospheric pressure of O2 to form the desired products with up to 97% isolated yield. The ability of Au/mesoporous alumina to catalyze these reactions under ambient conditions further enhances the sustainability of these chemical processes. Furthermore, the nanocatalyst was stable to air and water and could be recovered and reused easily. The enhanced catalytic activity of Au/mesoporous alumina might be attributed to the presence of negatively charged Au nanoparticles that could promote oxidation processes as well as the stability of the mesoporous alumina support calcined at a high temperature of 800°C. Gold for green: Gold nanoparticles supported on mesoporous alumina catalyze the efficient synthesis of amides and esters from simple building blocks of readily available alcohols and amines under ambient aerobic reaction conditions (R1=aryl, alkyl, and R2=H, alkyl).
