3559-04-4Relevant academic research and scientific papers
Rh(II)-catalyzed intermolecular oxidative sulfamidation of aldehydes: A mild efficient synthesis of N-sulfonylcarboxamides
Chan, Johann,Baucom, Kyle D.,Murry, Jerry A.
, p. 14106 - 14107 (2007)
Rh(II)-catalyzed oxidative coupling of aldehydes and sulfonamides has been developed to provide N-sulfonylcarboxamides in one step. A variety of sulfonamides were found to react with aromatic and aliphatic aldehydes to afford the desired products in good to excellent yields. Mechanistic data, including kinetic isotope effect experiments, suggest that the transformation proceeds through a concerted asynchronous nitrene insertion into an aldehydic hydrogen. Copyright
Bench-Stable Electrophilic Fluorinating Reagents for Highly Selective Mono- and Difluorination of Silyl Enol Ethers
Adachi, Akiya,Aikawa, Kohsuke,Ishibashi, Yuichiro,Nozaki, Kyoko,Okazoe, Takashi
supporting information, p. 11919 - 11925 (2021/07/02)
Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron-withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base-free conditions. Thus, both mono- and difluorinated target materials were prepared from the same substrate.
A Novel C–N Migration Rearrangement Based on N–F Compounds for the Synthesis of N-Alkyl Diaryl Ureas
Zhao, Yi-Xiao,Xie, Tian,Yang, San-Ke,Yang, Xian-Jin
, p. 437 - 445 (2020/01/22)
A novel rearrangement reaction based on the structure of N-fluoro-N-(phenylsulfonyl) benzamides (FPSBA) was developed. In the presence of base, unsymmetrical N-alkyl diaryl ureas were obtained in good yields which were accomplished through secondary alkyl phenylamines initiated 1,2-phenyl-shift migration rearrangement of N-fluoro-N-(phenylsulfonyl) benzamides. The reaction was carried out without using traditional, highly toxic reagents and noble metals. Whereas without rearrangement occurrence for primary phenylamines and aliphatic amines, normal amides and N-(phenylsulfonyl) benzamides were afforded respectively. Nitrene and phenyl isocyanate included process were prevented and a secondary alkyl phenylamine initiated vicinal SN2' reaction occurred. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operation, and useful products.
Facile synthesis of acyl sulfonamides from carboxyic acids using the Mukaiyama reagent
Chen, Ling,Luo, Guanglin
supporting information, p. 268 - 271 (2019/01/04)
A fast and convenient method using the Mukaiyama reagent was developed to prepare acyl sulfonamides from carboxylic acids and sulfonamides. This methodology is effective for a range of acids and sulfonamides proceeding in moderate to good yields with the
N-Sulfonyl acetylketenimine as a highly reactive intermediate for synthesis of N-Aroylsulfonamides
Yang, Weiguang,Huang, Dayun,Zeng, Xiaobao,Zhang, Jianlan,Wang, Xinyan,Hu, Yuefei
, p. 381 - 386 (2018/12/13)
A highly reactive intermediate N-sulfonyl acetylketenimine was generated from an ynone-participated CuAAC/ring-opening method. Its unique structure allowed it to react with aryl carboxylic acids to give N-aroylsulfonamides via a novel Mumm-type rearrangement.
Co-Catalyzed Synthesis of N-Sulfonylcarboxamides from Carboxylic Acids and Sulfonyl Azides
Fang, Yue,Gu, Zheng-Yang,Wang, Shun-Yi,Yang, Jin-Ming,Ji, Shun-Jun
, p. 9364 - 9369 (2018/07/09)
A Co-catalyzed effective synthesis of N-sulfonylcarboxamides from the reaction of carboxylic acids and organic azides in the presence of isocyanide has been developed. The protocol has the advantages of short time, low temperature, and being oxidant-free, which provides a new and simple approach for the synthesis of N-sulfonylcarboxamides in good to excellent yields with a broad substrate scope.
Ruthenium-Catalyzed Addition of Aromatic Amides to Internal Alkynes and Subsequent Intramolecular Cyclization for the Atom-Economical Synthesis of Isoindolinones
Miura, Hiroki,Terajima, Sachie,Tsutsui, Kentaro,Shishido, Tetsuya
, p. 1231 - 1239 (2018/06/18)
A selective and atom-economical synthesis of isoindolinones is described. This novel synthetic strategy involves two catalytic reactions: the ruthenium-catalyzed regioselective alkenylation of aromatic C-H bond of aromatic amides with internal alkynes, an
Catalytic activity of magnetic Fe3O4@Diatomite earth and acetic acid for the N-acylation of sulfonamides
Ghasemi, Mohammad Hadi,Kowsari, Elaheh,Hosseini, Seyed Kiumars
supporting information, p. 387 - 391 (2016/01/12)
The Br?nsted and Lewis acidic promoted N-acylation of sulfonamides with acetic anhydride or benzoyl chloride has been achieved using glacial acetic acid and magnetic Fe3O4@Diatomite earth. Use of acetic acid as solvent omits the need for organic bases and permits the isolation of products by filtration and precipitation. Additionally, the magnetic composite Fe3O4@Diatomite acts as a conjugate proton super acid, enabling the acylation of sulfonamide compounds.
Acidylation method of amine
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Paragraph 0036, (2016/10/10)
The invention discloses an acidylation method of amine.The method includes the following steps that amine derivatives, hydrazide derivatives, organic peroxide and a catalyst are dissolved in a solvent and react at the temperature of 40-80 DEG C, and amide derivatives are obtained.The amide derivatives and hydrazide derivatives serve as initiators, the raw materials are easy to obtain and the number of varieties is large.Products obtained through the method are diverse in type, can be directly used and can also be used for other further reactions.The method is mild in reaction condition, simple in reaction operation and post-processing process, high in product yield and suitable for scale production.
Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines
Williamson, Kevin S.,Sawicki, James W.,Yoon, Tehshik P.
, p. 3524 - 3527 (2014/08/18)
We have developed a highly selective kinetic resolution of N-sulfonyl oxaziridines. This reaction utilizes an inexpensive and easily synthesized iron bis(oxazoline) catalyst to promote the efficient rearrangement of oxaziridines to the corresponding N-sulfonyl imides; no sacrificial reagents are required to effect this resolution. This process is readily translated to gram scale, which provides a practical method for the preparation of structurally diverse, enantiopure N-sulfonyl oxaziridines for use as reagents in organic synthesis.
