862876-04-8Relevant articles and documents
Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon
Yang, Hui-Yi,Yao, Ya-Hong,Chen, Ming,Ren, Zhi-Hui,Guan, Zheng-Hui
, p. 7298 - 7305 (2021/05/26)
Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.
TCFH-NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations
Beutner, Gregory L.,Young, Ian S.,Davies, Merrill L.,Hickey, Matthew R.,Park, Hyunsoo,Stevens, Jason M.,Ye, Qingmei
supporting information, p. 4218 - 4222 (2018/07/29)
Challenging couplings of hindered carboxylic acids with non-nucleophilic amines to form amide bonds can be accomplished in high yields, and in many cases, with complete retention of the adjacent stereogenic centers using the combination of N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI). This method allows for in situ generation of highly reactive acyl imidazolium ions, which have been demonstrated to be intermediates in the reaction. The reagent delivers high reactivity similar to acid chlorides with the ease of use of modern uronium reagents.
Visible Light-Induced Radical Rearrangement to Construct C-C Bonds via an Intramolecular Aryl Migration/Desulfonylation Process
Li, Yuyuan,Hu, Bei,Dong, Wuheng,Xie, Xiaomin,Wan, Jun,Zhang, Zhaoguo
, p. 7036 - 7041 (2016/08/30)
A highly efficient intramolecular selective aryl migration/desulfonylation of 2-bromo-N-aryl-N-(arenesulfonyl)amide via visible light-induced photoredox catalysis has been accomplished. This approach allows for the construction of a variety of multisubstituted N,2-diarylacetamide under mild reaction conditions.
DBU catalysis of N,N'-carbonyldiimidazole-mediated amidations
Larrlvee-Aboussafy, Claude,Jones, Brian P.,Price, Kristin E.,Hardink, Mark A.,McLaughlin, Robert W.,Lillie, Brett M.,Hawkins, Joel M.,Vaidyanathan, Rajappa
supporting information; experimental part, p. 324 - 327 (2010/03/24)
(Figure presented) 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) has been found to catalyze the amidatlon of acyl imidazoles. The rate acceleration is especially evident with traditionally unreactlve, electron-deficient anilines. DBU is readily available and o
A comparison of catalysts to promote imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst
Dunn, Peter J.,Hoffmann, Wilfried,Kang, Ying,Mitchell, John C.,Snowden, Martin J.
, p. 956 - 961 (2012/12/26)
Five catalysts were compared with respect to their safety and catalytic effectiveness for promoting imidazolide couplings. Reaction rate enhancement, shock sensitivity, and differential scanning calorimetry (DSC) data were considered in this analysis. 6-Chloro-1-hydroxybenzotriazole, which has been described in the literature as a safe catalyst, was found to be shock sensitive. 2-Hydroxy-5-nitropyridine is a new catalyst for this type of reaction and was found to be safe, effective, readily available, and similar in price to that of the 1-hydroxybenzotriazole, a common catalyst for promoting acylation reactions.
