- Synthesis of imides via palladium-catalyzed three-component coupling of aryl halides, isocyanides and carboxylic acids
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A palladium-catalyzed three-component synthesis of acyclic imides from feedstock aryl halides, carboxylic acids and isocyanides through the intermediacy of isoimides has been developed. The key to the success of this approach was controlled isocyanide slow addition and organic/aqueous biphasic conditions. This transition-metal-catalyzed approach features readily available starting materials, atom- and step-economy, good functional group compatibility and gram-scale synthetic capability. Utilization of this new method is illustrated in the late-stage functionalization of drugs Carprofen, Loxoprofen and Flurbiprofen. This strategy has also been successfully applied in the synthesis of cyclic imides including phthalimide, homophthalimide, and 2H-2-benzazepine-1,3-dione derivatives.
- Wang, Bo,He, Dan,Ren, Beige,Yao, Tuanli
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supporting information
p. 900 - 903
(2020/02/03)
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- Synthetic method for N-substituted imide
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The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.
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Paragraph 0016; 0022; 0023; 0024; 0025
(2017/04/20)
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- Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion
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A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields.
- Wang, Xu,Xiong, Wenfang,Huang, Yubing,Zhu, Jiayi,Hu, Qiong,Wu, Wanqing,Jiang, Huanfeng
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p. 5818 - 5821
(2017/11/10)
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- Method for preparing 2-substituted-isoindole-1,3-dione derivative
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The invention relates to a method for preparing a 2-substituted-isoindole-1,3-dione derivative. A 2-alkynyl benzaldehyde compound and primary amine serve as reaction raw materials, and the 2-substituted-isoindole-1,3-dione derivative is obtained at high yield under the condition that copper salt serves as a catalyst. The method has the advantages that a synthesis route is simple, reaction conditions are mild, a substrate application range is wide, the yield is high, the reaction process is easy to control, and implementation performance is high.
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Paragraph 0021; 0025
(2017/05/09)
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- Visible-light induced isoindoles formation to trigger intermolecular diels-alder reactions in the presence of air
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Visible-light induced isoindole formation triggered an intermolecular Diels-Alder reaction with dienophiles such as acetylenedicarboxylate and maleimides in the presence of air. The reaction resulted in excellent diastereoselctivity and high yields under
- Lin, Chao,Zhen, Le,Cheng, Yong,Du, Hong-Jin,Zhao, Hui,Wen, Xiaoan,Kong, Ling-Yi,Xu, Qing-Long,Sun, Hongbin
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supporting information
p. 2684 - 2687
(2015/06/16)
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- Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
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Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.
- Wang, Min,Lu, Jianmin,Ma, Jiping,Zhang, Zhe,Wang, Feng
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supporting information
p. 14061 - 14065
(2016/01/25)
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- Ruthenium(II)-Catalyzed C-H Activation with Isocyanates: A Versatile Route to Phthalimides
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A cationic ruthenium(II)-complex was utilized in the efficient synthesis of phthalimide derivatives by C- H activation with synthetically useful amides. The reaction proceeded through a mechanistically unique insertion of a cycloruthenated species into a C- Het multiple bond of isocyanate. The novel method also proved applicable for the synthesis of heteroaromatic unsymmetric diamides as well as a potent COX-2 enzyme inhibitor. A convenient route to phthalimide: A convergent method for the ruthenium(II)-catalyzed imidation of easily accessible benzamides by C- H functionalization was developed (see scheme). The methodology was successfully applied to the preparation of synthetically challenging unsymmetrical heteroaromatic diamides and proved amenable to a step-economic synthesis of a potent COX-2 enzyme inhibitor.
- Desarkar, Suman,Ackermann, Lutz
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supporting information
p. 13932 - 13936
(2016/02/18)
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- A rhodium-catalyzed cascade cyclization: Direct synthesis of N-substituted phthalimides from isocyanates and benzoic acids
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A rhodium(III)-catalyzed amidation between benzoic acids and isocyanates via direct functionalization of an ortho C-H bond followed by intramolecular cyclization is described. This cascade cyclization affords N-substituted phthalimides in one step in 26-91% yields. The reaction is highly atom-economical, since no theoretical waste except for water is generated in the reaction.
- Shi, Xian-Ying,Renzetti, Andrea,Kundu, Soumen,Li, Chao-Jun
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supporting information
p. 723 - 728
(2014/04/03)
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- Palladium-catalyzed carbonylation and coupling reactions of aryl chlorides and amines
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The palladium-catalyzed amidation of electron-deficient aryl chlorides proceeds readily in the presence of low CO pressures and a slight excess of an iodide salt. The rates of amidation are accelerated over those without added salt, and iodide is preferred over bromide or chloride. More electron-rich aryl chlorides were not effectively amidated, either with or without added iodide. We postulate that an intermediate anionic palladium(0) iodide complex is responsible for the enhanced reactivity.
- Perry, Robert J.,Wilson, B. David
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p. 7482 - 7485
(2007/10/03)
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- Preparation of N-Substituted Phthalimides by Palladium-Catalyzed Carbonylation and Coupling of o-Dihalo Aromatics and Primary Amines
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A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines.Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115 deg C, 90 psi of CO, 3 percent PdCl2L2, and 2.4 equiv of DBU.This process is tolerant of a wide variety of functional groups and gives good yields of the desired products.Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction.The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.
- Perry, Robert J.,Turner, S. Richard
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p. 6573 - 6579
(2007/10/02)
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- Synthesis of certain bis(phthalic anhydrides)
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Monomeric high molecular weight dianhydrides or tetraacids can be produced by the nucleophilic coupling of a halo substituted phthalimides acid and an aliphatic or aromatic compound having polyfunctional groups capable of reacting with the halo moiety of the phthalinide followed by hydrolysis and dehydration. Specifically, 4-chlorophthalate sodium salt is converted to an imide to reduce side reactions with the carboxylic acid groups prior to reaction with 4,4'-disodiumdiphenylene oxide sulfone or 2,2-di (4-sodium phenoxide) propane. After the reaction of the imide and the sulfone or propane compounds, the diimide formed is converted to the corresponding dianhydride.
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