19523-30-9Relevant academic research and scientific papers
Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature
Jiang, Hezhong,Li, Jiahong,Li, Jun-Long,Lin, Li,Liu, Jianchen,Liu, Xiang-Wei,Wang, Jingxia,Yang, Zhonglie,Zhang, Xiaobin,Zheng, Jiale
supporting information, p. 5467 - 5473 (2021/08/16)
A green and efficient visible-light-induced iodosulfonyl reaction of alkenes in water using an EDA complex strategy at room temperature has been disclosed. The addition of a cationic surfactant allows for the easy formation of colored EDA complexes in water. The hydrophobic effect of the core in the surfactant aggregates, which act as a reaction medium formed by the surfactants themselves in water, plays a significant role in stabilizing the transition state and decreasing the activation energy of the reaction. Remarkably, transition-metal catalysts and organic solvents were not required in this transformation. Moreover, it displayed a broad substrate scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of β-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.
Copper-Catalyzed Chloro-Arylsulfonylation of Styrene Derivatives via the Insertion of Sulfur Dioxide
Li, Yue,Shen, Lin,Zhou, Mi,Xiong, Baojian,Zhang, Xuemei,Lian, Zhong
supporting information, p. 5880 - 5884 (2021/08/01)
A copper-catalyzed four-component chloro-arylsulfonylation of styrene derivatives with aryldiazonium tetrafluoroborates, lithium chloride, and ex-situ generated sulfur dioxide (from SOgen) is presented. This sulfonylation features good functional group compatibility, mild reaction conditions, excellent regioselectivity, and good yields. The robustness and potential of this method have also been successfully demonstrated by a gram-scale reaction. Based on experimental study, a radical-involved mechanism is proposed for the transformation.
Visible light promoted sulfonylation and sulfonylcarbonylation of alkenes
Min, Wenjian,Guo, Guozhe,Yang, Caixia,Huo, Congde
, (2020/05/26)
Visible light promoted sulfonylation and sulfonylcarbonylation reactions of readily available alkenes with TosMIC for the synthesis of valuable vinyl sulfones and β-keto sulfones were described. A reasonable radical involved mechanism is proposed.
N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature
Hu, Yuefei,Luo, Dongping,Min, Lin,Shan, Lidong,Wang, Xinyan,Zheng, Weiping
, (2020/02/18)
N,N′-Disulfonylhydrazines have been proven to be the most reactive precursors of sulfonyl radicals in all types of sulfonyl substituted hydrazines as early as a half century ago. But such function has not been applied in organic synthesis except the formation of disulfones by self-dimerization of sulfonyl radicals. In this article, they were introduced as new sulfonylating reagents and their combinations with NIS and Et3N were established as excellent iodosulfonylating reagents for alkenes. Finally, a highly efficient method for the synthesis of (E)-vinyl sulfones was developed by mixing an alkene, a N,N′-disulfonylhydrazine, NIS and Et3N in THF at room temperature for 5 min.
A convenient access to β-iodo sulfone by the iodine-mediated iodosulfonylation of alkenes
Sun, Kai,Lv, Yunhe,Zhu, Zhonghong,Jiang, Yongqing,Qi, Jiejie,Wu, Hankui,Zhang, Zhiguo,Zhang, Guisheng,Wang, Xin
, p. 50701 - 50704 (2015/06/25)
A novel iodine-mediated intermolecular iodosulfonylation reaction of alkenes for dual C-S and C-I bond formation is described. A series of alkenes could be selectively converted into the corresponding β-iodo sulfones, which are versatile building blocks in organic synthesis and medicinal chemistry. Molecular iodine was the iodine source in this reaction.
PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones
Katrun, Praewpan,Chiampanichayakul, Supanimit,Korworapan, Kanokwan,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Kuhakarn, Chutima
scheme or table, p. 5633 - 5641 (2010/12/25)
(Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yield
CONVENIENT METHODS FOR THE PREPARATION OF VINYLIC AND ALLYLIC SULFONES FROM ALKENES
Inomata, Katsuhiko,Kobayashi, Toshifumi,Sasaoka, Shin-ichi,Kinoshita, Hideki,Kotake, Hiroshi
, p. 289 - 292 (2007/10/02)
1 or 2-p-Toluenesulfonyl(=tosyl)-1-alkenes were regioselectively prepared from 1-alkenes via iodosulfonization or sulfonylmercuration, respectively.Conversion of 1-tosyl-1-alkenes to the corresponding allylic sulfones, 1-tosyl-2-alkenes, was achieved by t
Copper-Catalyzed Additions of Sulfonyl Iodides to Simple and Cyclic Alkenes
Liu, Lilian Kao,Chi, Y.,Jen, Kwan-Yue
, p. 406 - 410 (2007/10/02)
A convenient synthesis for various β-iodo sulfones has been developed.The reaction involves additions of alkane- and arenesulfonyl iodides to simple and cyclic alkenes under the catalytic action of copper(II) chloride.The favored stereochemical results for cyclic alkenes have been rationalized in terms of stepwise addition of both portions of the addend from the diaxial direction.
