52720-03-3Relevant articles and documents
Rhodium(iii)-catalyzed cascade C-H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines
Chen, Lu,Hao, Liqiang,Ji, Yafei,Wang, Yangyang,Wang, Zhichao,Wu, Gaorong,Xu, Xiaobo
supporting information, p. 887 - 894 (2022/02/03)
A highly efficient Rh(iii)-catalyzed cascade C-H activation/annulation of sulfoximines with iodonium ylides under metal-oxidant-free conditions has been reported. The fused cyclohexanone-1,2-benzothiazine scaffold is readily achieved with a one-pot proces
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.
Synthesis and Configurational Assignment of Vinyl Sulfoximines and Sulfonimidamides
Craven, Gregory B.,Briggs, Edward L.,Zammit, Charlotte M.,McDermott, Alexander,Greed, Stephanie,Affron, Dominic P.,Leinfellner, Charlotte,Cudmore, Hannah R.,Tweedy, Ruth R.,Luisi, Renzo,Bull, James A.,Armstrong, Alan
, p. 7403 - 7424 (2021/06/25)
Vinyl sulfones and sulfonamides are valued for their use as electrophilic warheads in covalent protein inhibitors. Conversely, the S(VI) aza-isosteres thereof, vinyl sulfoximines and sulfonimidamides, are far less studied and have yet to be applied to the field of protein bioconjugation. Herein, we report a range of different synthetic methodologies for constructing vinyl sulfoximine and vinyl sulfonimidamide architectures that allows access to new areas of electrophilic chemical space. We demonstrate how late-stage functionalization can be applied to these motifs to incorporate alkyne tags, generating fully functionalized probes for future chemical biology applications. Finally, we establish a workflow for determining the absolute configuration of enantioenriched vinyl sulfoximines and sulfonimidamides by comparing experimentally and computationally determined electronic circular dichroism spectra, enabling access to configurationally assigned enantiomeric pairs by separation.
Electrochemical Oxidative Syntheses of NH-Sulfoximines, NH-Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates
Kong, Xianqiang,Lin, Long,Chen, Xiaohui,Chen, Yiyi,Wang, Wei,Xu, Bo
, p. 3277 - 3282 (2021/07/26)
Herein, we report a general method for the synthesis of NH-sulfoximines and NH-sulfonimidamides through direct electrochemical oxidative catalysis involving an iodoarene(I)/iodoarene(III) redox couple. In addition, dibenzothiazines can be synthesized from [1,1′-biaryl]-2-sulfides under standard conditions. Notably, only a catalytic amount of iodoarene is required for the generation in situ of an active hypervalent iodine catalyst, which avoids the need for an excess of a hypervalent iodine reagent relative to conventional approaches. Moreover, this protocol features broad substrate scope and wide functional group tolerance, delivering the target compounds with good-to-excellent yields even for a scale of more than 10 g.
Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis
Liu, Dong,Liu, Zhao-Ran,Ma, Cong,Jiao, Ke-Jin,Sun, Bing,Wei, Lei,Lefranc, Julien,Herbert, Simon,Mei, Tian-Sheng
supporting information, p. 9444 - 9449 (2021/03/29)
A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C?N bond from the resulting NiIII species at room temperature.
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/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines
Li, Jian,Li, Hui,Fang, Daqing,Liu, Lingjun,Han, Xu,Sun, Jina,Li, Chunpu,Zhou, Yu,Ye, Deju,Liu, Hong
, p. 15217 - 15227 (2021/10/25)
A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.
Synthesis of NH-Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions
Zhang, Guocai,Tan, Hongsheng,Chen, Weichun,Shen, Hong C.,Lu, Yue,Zheng, Changwu,Xu, Hongxi
, p. 922 - 928 (2020/02/20)
The synthesis of NH-sulfoximines from sulfides has been first developed under mild conditions in an aqueous solution with surfactant TPGS-750-M as the catalyst at room temperature. In this newly developed process, a simple and convenient recycling strategy to regenerate the indispensable hypervalent iodine(III) is used. The resulting 1,2,3-trifluoro-5-iodobezene can be recovered almost quantitively from the mixture by liquid–liquid extraction and then oxidized to give the corresponding iodine(III) species. This optimized procedure is compatible with a broad range of functional groups and can be easily performed on a gram scale, providing a green protocol for the synthesis of sulfoximines.
Palladium-Catalyzed Oxidative Annulation of Sulfoximines and Arynes by C-H Functionalization as an Approach to Dibenzothiazines
Li, Jing,Li, Shan,Liu, Liansheng,Wang, Rong,Wei, Junfa,Yang, Yihui
supporting information, p. 7470 - 7474 (2020/10/09)
This work reports a novel and efficient palladium-catalyzed synthesis of tricyclic dibenzothiazines using easily prepared aryl sulfoximines and aryne precursors via C-H functionalization and cyclization. A mechanistic investigation indicated that the C-H bond cleavage at the position ortho to the sulfoximine group is the rate-determining step.
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.
