2618-96-4Relevant articles and documents
Merging Photoredox Catalysis with Transition Metal Catalysis: Direct C4-H Sulfamidation of 1-Naphthylamine Derivatives
Pei, Mengxue,Zu, Conghui,Liu, Zhen,Yang, Fan,Wu, Yangjie
, p. 11324 - 11332 (2021/09/02)
A mild and efficient protocol for the copper(I)-catalyzed C4-H sulfamidation of 1-naphthylamine derivatives with diphenylsulfonimide (NHSI) was explored at room temperature, affording the desire produces in moderate to good yields. The control experiments indicated that this visible-light-promoted reaction might proceed via a single-electron-transfer process. In addition, preliminary DFT studies for the intermediates in the catalytic cycle were also explored, indicating that the C4 site in the naphthyl ring is the most likely electrophilic reactive site and providing some exact basis for the plausible mechanism.
Cobalt-catalyzed Divergent Markovnikov and Anti-Markovnikov Hydroamination
Chen, Zheng,Guo, Peng,He, Zi-Xin,Ye, Ke-Yin,Zhang, Xiang-Gui
supporting information, (2022/01/04)
Catalytic hydroamination of the readily available alkenes is among the most straightforward means to construct diverse alkyl amines. To this end, the facile access to both regioselectivity, i.e., Markovnikov or anti-Markovnikov hydroamination, with minimum reaction-parameter alternation, remains challenging. Herein, we report a cobalt-catalyzed highly selective and divergent Markovnikov and anti-Markovnikov hydroamination of alkenes, in which the switch of regioselectivity is achieved simply by the variation of the addition sequence of 9-BBN.
Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant
Yi, Xuewen,Yi, Xuewen,Lei, Siyu,Liu, Wangsheng,Che, Fengrui,Yu, Chunzheng,Liu, Xuesong,Wang, Zonghua,Zhou, Xin,Zhang, Yuexia
supporting information, p. 4583 - 4587 (2020/05/05)
An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
A Novel Synthesis of N -Sulfonylformamidines from N Sulfonyl sulfonamides
Jeong, Yuri,Ban, Jaeyoung,Lim, Minkyung,Rhee, Hakjune
supporting information, p. 1867 - 1874 (2018/02/26)
N -Sulfonylformamidines were synthesized from N -sulfonylsulfonamides by reacting with p -toluenesulfonyl chloride (TsCl) and N, N - disubstituted formamides. In this reaction, it was expected that mixing TsCl with the N, N -disubstituted formamide would generate an iminium salt (Vilsmeier reagent). The reaction avoids the use of metal catalysts and hazardous reagents, and the desired N -sulfonylformamidines were obtained in 60% to quantitative yields.
Synergistic copper-TEMPO catalysis of intermolecular vicinal diamination of styrenes
Weng, Shiue-Shien,Hsieh, Kun-Yi,Zeng, Zih-Jian,Zhang, Jia-Wei
supporting information, p. 670 - 673 (2017/01/25)
A copper-catalyzed, 2,2,6,6-tetramethyl piperidine N-oxy radical-assisted intermolecular diamination of styrenes with N-fluorobenzenesulfonimide has been developed. The current protocol proved amenable to a diverse array of styrenes via cascade radical addition to readily afford synthetically useful aromatic vicinal diamines with exclusive diastereoselectivity.
Method for preparing dibenzenesulfonimide by solvent-free grinding method
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Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024-0027, (2017/08/28)
The invention relates to a method for preparing dibenzenesulfonimide by a solvent-free grinding method. According to the method, firstly, benzsulfamide and pure benzene sulfonyl chloride are put into a ball mill to be ground, so that the benzsulfamide and the benzene sulfonyl chloride are sufficiently and uniformly mixed at room temperature; then, solid NaOH is fed into the ball mill in different batches; the grinding is continuously performed; the temperature of a reactant is maintained to be lower than 60 DEG C; after the reaction is completed, the reactant is moved out from the ball mill; the reactants are dissolved by organic solvents; filtering is performed for removing generated NaCl; filter liquid is obtained; finally, the filter liquid is subjected to concentration crystallization, filtering and drying; a product is obtained. In the whole reaction process, the solvent is not needed; the environment pollution is reduced; the production cost is reduced. The atom utilization rate of the whole preparation process is high; the atom economic green and environment-friendly ideal is met; the method is suitable for industrial production.
Preparation method of dibenzenesulfonimide
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Paragraph 0032; 0033, (2017/02/09)
The invention discloses a preparation method of dibenzenesulfonimide. The preparation method comprises the following steps: (1) preparing dibenzenesulfonimide sodium salt: adding benzene sulfonamide and benzene sulfonyl chloride into an isopropanol-sodium alcoholate system in different steps to carry out reactions; (2) purifying dibenzenesulfonimide sodium salt: adding sodium hydroxide into the isopropanol-sodium alcoholate system in different steps, adjusting the pH value to 10-12, making the system go through anion exchange resin, then cooling to precipitate crystals, and carrying out centrifugal separation to obtain dibenzenesulfonimide sodium salt; (3) preparing dibenzenesulfonimide: dissolving dibenzenesulfonimide sodium salt into hot water, making the solution go through cation exchange resin, cooling to precipitate crystals, carrying out centrifugal separation, and drying to obtain dibenzenesulfonimide. The preparation method has the advantages that raw materials are fully and effectively converted into the target product, the side reactions are avoided, the purification and separation mode is reasonable, the product purity is high, the yield is high, and moreover, the method is economic and environment-friendly and can be easily applied to industrial production.
PROCESS FOR THE PREPARATION OF DIBENZENESULFONIMIDE
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Page/Page column 6, (2016/02/26)
The present invention provides a process for the preparation of dibenzenesulfonimide.
N-Trifluoromethylthio-dibenzenesulfonimide: A Shelf-Stable, Broadly Applicable Electrophilic Trifluoromethylthiolating Reagent
Zhang, Panpan,Li, Man,Xue, Xiao-Song,Xu, Chunfa,Zhao, Qunchao,Liu, Yafei,Wang, Haoyang,Guo, Yinlong,Lu, Long,Shen, Qilong
, p. 7486 - 7509 (2016/09/09)
The super electrophilicity of a shelf-stable, easily prepared trifluoromethylthiolating reagent N-trifluoromethylthio-dibenzenesulfonimide 7 was demonstrated. Consistent with the theoretical prediction, 7 exhibits reactivity remarkably higher than that of other known electrophilic trifluoromethylthiolating reagents. In the absence of any additive, 7 reacted with a wide range of electron-rich arenes and activated heteroarenes under mild conditions. Likewise, reactions of 7 with styrene derivatives can be fine-tuned by simply changing the reaction solvents to generate trifluoromethylthiolated styrenes or oxo-trifluoromethylthio or amino-trifluoromethylthio difunctionalized compounds in high yields.
Highly regioselective radical amination of allenes: Direct synthesis of allenamides and tetrasubstituted alkenes
Zhang, Ge,Xiong, Tao,Wang, Zining,Xu, Guoxing,Wang, Xuedan,Zhang, Qian
supporting information, p. 12649 - 12653 (2015/10/28)
The first controllable, regioselective radical amination of allenes with N-fluoroarylsulfonimide is described to proceed under very mild reaction conditions. With this methodology, a general and straightforward route for the synthesis of both allenamides and fluorinated tetrasubstituted alkenes was realized from a wide range of terminal and internal allenes. Radical highway: By employing N-fluoroarylsulfonimide as a nitrogen source, a facile, mild, and highly regioselective copper-catalyzed oxidative radical amination of various allenes was developed. In addition, a protocol involving nitrogen radical addition/fluorine-atom transfer affords fluorinated tetrasubstituted alkenes by using silver as catalyst.
