5215-40-7Relevant academic research and scientific papers
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.
Rhodium-Catalyzed Synthesis of Amides from Functionalized Blocked Isocyanates
Beauchemin, André M.,Derasp, Joshua S.
, p. 8104 - 8109 (2019/08/26)
Isocyanates are useful building blocks for the synthesis of amides, although their widespread use has been limited by their high reactivity, which often results in poor functional group tolerance and a propensity to oligomerize. Herein, a rhodium-catalyzed synthesis of amides is described coupling boroxines with blocked (masked) isocyanates. The success of the reaction hinges on the ability to form both the isocyanate and the organorhodium intermediates in situ. Relying on masked isocyanate precursors and on the high reactivity of the organorhodium intermediate results in broad functional group tolerance, including protic nucleophilic groups such as amines, anilines, and alcohols.
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.
Visible-Light-Promoted C-H Arylation by Merging Palladium Catalysis with Organic Photoredox Catalysis
Jiang, Jian,Zhang, Wen-Man,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 3622 - 3630 (2017/04/11)
The use of a dual palladium/organic photoredox catalytic system enables the directed arylation of arenes with aryldiazonium salts with a broad substrate scope at room temperature under mild reaction conditions. This study thus serves as not only an alternative route for the biaryl motifs but also a new example for the application of an organic photoredox catalyst.
Amine Activation: Synthesis of N-(Hetero)arylamides from Isothioureas and Carboxylic Acids
Zhu, Yan-Ping,Sergeyev, Sergey,Franck, Philippe,Orru, Romano V. A.,Maes, Bert U. W.
supporting information, p. 4602 - 4605 (2016/09/28)
A novel method for N-(hetero)arylamide synthesis based on rarely explored amine activation, rather than classical acid activation, is reported. The activated amines are easily prepared using a three-component reaction with commercial reagents. The new method shows a broad scope including challenging amides not (efficiently) accessible via classical protocols.
Copper-Catalyzed sp3 C-H Aminative Cyclization of 2-Alkyl-N-arylbenzamides: An Approach for the Synthesis of N-Aryl-isoindolinones
Nozawa-Kumada, Kanako,Kadokawa, Jun,Kameyama, Takehiro,Kondo, Yoshinori
supporting information, p. 4479 - 4481 (2015/09/28)
The synthesis of isoindolinones via copper-catalyzed sp3 C-H functionalization of 2-alkyl-N-substituted benzamides is described. This process does not require the preparation of halogenated substitutes, expensive transition metals, or toxic Sn or CO gas. This method provides an efficient approach to generate various functionalized isoindolinones.
Metal-free synthesis of amides by oxidative amidation of aldehydes with amines in PEG/oxidant system
Liang, Jun,Lv, Jing,Shang, Zhi-Cai
supporting information; experimental part, p. 8532 - 8535 (2011/11/12)
A simple, inexpensive, and efficient one-pot synthesis of amide derivatives were achieved in good to excellent yields via the directly oxidative amidation of aldehydes with amines under PEG/Oxidant system.
Synthesis of amides through the Cannizzaro-type reaction catalyzed by lanthanide chlorides
Zhang, Lijun,Su, Shunpeng,Wu, Hongping,Wang, Shaowu
supporting information; experimental part, p. 10022 - 10024 (2010/02/27)
Amidation of aldehydes with lithium amides through the LnCl3-catalyzed Cannizzaro-type reactions afforded a variety of amides in high yields. The electronic and steric effects on the reaction were investigated. The features of the economical ca
Steric effects of polymethylcarboranes. Unusual reactivity of N-(deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl)pyridinium
Yaguchi, Kyoko,Endo, Yasuyuki
, p. 7351 - 7354 (2007/10/03)
Reaction of deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl chloride with aniline in pyridine gives predominantly deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carboxamide, accompanied by a small amount of the expected anilide. The results may be interpreted in terms of nucleophilic attack of aniline at the 2'-position of the N-(deca-B-methyl-1,12-dicarba-closo-dodecaborane-1-carbonyl)pyridinium intermediate, followed by ring-opening of the pyridine nucleus and recyclization.
Zur Chemie des Dimesityleisens. VII. Die Reaktionen von Dimesityleisen mit Isocyanaten und Isothiocyanaten; Struktur des Produkts mit Phenylisocyanat
Mueller, Hardy,Seidel, Wolfgang,Goerls, Helmar
, p. 215 - 220 (2007/10/02)
The reaction of 2> with the compounds Ph-NCO, Cy-NCO, 2-Naphth-NCO and Ph-NCS proceeds with insertion into all Fe-C-bonds.The structure of the compound 2>3>(THF) is determined.After hydrolysis the corresponding amides
