76456-06-9Relevant academic research and scientific papers
Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes
Amri, Nasser,Wirth, Thomas
, p. 15961 - 15972 (2021/07/20)
An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides toN-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, andN-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.
One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
Zupanc, An?e,Jereb, Marjan
, p. 5991 - 6000 (2021/05/05)
This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.
Blue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes
Chen, Hongyi,Chen, Li,He, Ze,Zeng, Qingle
supporting information, p. 2624 - 2627 (2021/04/21)
A transition metal-free synthesis ofN-(arylthio/seleno)ethyl sulfoxidminesviablue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes was developed. The sulfoximidation process demonstrated high chemoselectivity and allowed a broad substrate scope, completing the sulfoximido-chalcogenization of alkenes in good yields.
Sulfoximines-assisted Rh(III)-catalyzed C-H activation and intramolecular annulation for the synthesis of fused isochromeno-1,2-benzothiazines scaffolds under room temperature
Han, Xu,Li, Chunpu,Li, Jian,Liu, Hong,Wang, Bao
, (2020/06/29)
Amild and facile Cp?Rh(III)-catalyzed C-Hactivation and intramolecular cascade annulation protocol has been proposed for the furnishing of highly fused isochromeno-1,2-benzothiazines scaffolds using S-phenylsulfoximides and 4-diazoisochroman-3-imine as substrates under room temperature. This method features diverse substituents and functional groups tolerance and relatively mild reaction conditions with moderate to excellent yields. Additionally, retentive configuration of sulfoximides in the conversion has been verified.
Palladium-Catalyzed Electrochemical C-H Bromination Using NH4Br as the Brominating Reagent
Yang, Qi-Liang,Wang, Xiang-Yang,Wang, Tong-Lin,Yang, Xiang,Liu, Dong,Tong, Xiaofeng,Wu, Xin-Yan,Mei, Tian-Sheng
supporting information, p. 2645 - 2649 (2019/04/17)
The palladium-catalyzed electrochemical C-H bromination of benzamide derivatives under divided cells is developed, in which NH4Br serves as a brominating reagent and electrolyte. The protocol avoids the use of chemical oxidants and provides an alternative method for the synthesis of aryl bromides.
Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides
Yu, Hao,Li, Zhen,Bolm, Carsten
supporting information, p. 324 - 327 (2017/12/15)
Free NH-sulfoximines were directly prepared from sulfoxides through iron catalysis by applying a readily available, shelf-stable hydroxylamine triflic acid salt. No additional oxidant is needed, and the substrate scope is broad, including a range of heter
Ru (II)-Catalyzed Coupling-Cyclization of Sulfoximines with alpha-Carbonyl Sulfoxonium Ylides as an Approach to 1,2-Benzothiazines
Xie, Haisheng,Lan, Jianyong,Gui, Jiao,Chen, Fengjuan,Jiang, Huangfeng,Zeng, Wei
, p. 3534 - 3543 (2018/08/06)
A Ru(II)-catalyzed approach for the rapid assembly of 1,2-benzothiazines has been developed to enable the coupling-cyclization of aryl Csp2?H bonds with α-carbonyl sulfoxonium ylides via Csp2?H activation process. The present method could be further applied to the construction of the 4-substituted 1,2-benzothiazine skeletons. (Figure presented.).
Eaton's reagent-mediated metal-free and efficient synthesis of NH-sulfoximines
Wang, Jianping,Zhang, Jian,Miao, Kun,Yun, Hongying,Shen, Hong C.,Zhao, Weili,Liang, Chungen
supporting information, p. 333 - 337 (2017/01/03)
NH-sulfoximines can be prepared efficiently from corresponding sulfoxides in the presence of sodium azide and Eaton's reagent. This metal-free and efficient methodology is applicable to a wide variety of functionalized sulfoxides to afford NH-sulfoximines in good to excellent yields with shorter reaction time than previously reported methods.
A Convenient, Mild, and Green Synthesis of NH-Sulfoximines in Flow Reactors
Degennaro, Leonardo,Tota, Arianna,De Angelis, Sonia,Andresini, Michael,Cardellicchio, Cosimo,Capozzi, Maria Annunziata,Romanazzi, Giuseppe,Luisi, Renzo
, p. 6486 - 6490 (2017/09/13)
NH-sulfoximines are emerging as useful and important targets in drug discovery and synthetic organic chemistry. We report herein the development of an efficient, convenient, and sustainable continuous-flow strategy, for the direct, straightforward preparation of NH-sulfoximines by using sulfides or sulfoxides as suitable starting material. The flow process uses PhI(OAc)2 as the oxidant and aqueous solutions of ammonia as the N source. The scope of the reaction has been demonstrated by using several substituted sulfides and sulfoxides including enantioenriched and biologically relevant starting materials. The flow strategy was found to be more convenient with respect to conventional batch processing.
Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence for λ6-sulfanenitrile intermediates
Lohier, Jean-Fran?ois,Glachet, Thomas,Marzag, Hamid,Gaumont, Annie-Claude,Reboul, Vincent
supporting information, p. 2064 - 2067 (2017/02/15)
We report a new procedure for the preparation of NH-sulfoximines from sulfides using PIDA as an oxidant and ammonium carbamate as the ammonia source. Excellent yields were obtained with a wide range of sulfides. The formation of acetoxy- and methoxy-λsup
