14910-16-8Relevant academic research and scientific papers
Visible-light promoted aerobic difunctionalization of alkenes with sulfonyl hydrazides for the synthesis of β-keto/hydroxyl sulfones
Wu, Jie,Zhang, Yulan,Gong, Xinchi,Meng, Yunge,Zhu, Chunyin
supporting information, p. 3507 - 3513 (2019/04/14)
A practical method has been developed for the conversion of alkenes to β-keto/hydroxyl sulfones by their reaction with sulfonyl hydrazides under metal-free conditions. This reaction proceeds through the oxidative addition of alkenes by sulfonyl radicals that are generated by visible-light induced oxidation of sulfonyl hydrazides. Notaly the reaction uses O2 as the terminal oxidant, instead of metal catalysts or oxidants like TBHP, leading to H2O and N2 as the clean by-products. The key features of this reaction include readily available reagents, mild reaction conditions and broad substrate scope.
Method for preparing beta-keto sulfone or beta-hydroxy sulfone from reaction of substituted olefin and sulfonyl hydrazine derivative
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Paragraph 0017; 0018; 0023; 0024; 0025; 0026, (2019/02/06)
The invention belongs to the technical field of organic chemical synthesis and specifically relates to a method for preparing beta-keto sulfone or beta-hydroxy sulfone from reaction of substituted olefin and sulfonyl hydrazine derivative. The method comprises the following steps: taking substituted olefin and sulfonyl hydrazine derivative as raw materials, taking air as an oxidizing agent and performing oxidizing addition reaction under the existence of photosensitizer and alkali and under the condition of visible light irradiation, thereby generating beta-keto sulfone or beta-hydroxy sulfone.The method provided by the invention is low in cost of raw materials, simple in process, green and safe, efficient and environment-friendly, and suitable for industrial production.
α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization
Kanyiva, Kyalo Stephen,Hamada, Daisuke,Makino, Sohei,Takano, Hideaki,Shibata, Takanori
, p. 5905 - 5909 (2018/09/14)
We developed a silver-catalyzed strategy for the generation of sulfonyl radicals from sulfonamides derived from α-amino acids. The reaction proceeded via a decarboxylation, N–S bond cleavage and radical cyclization sequence and allows the difunctionalization of alkynes and the synthesis of 3-sulfonylated coumarins. The reaction tolerated a broad scope of substrates and functional groups and could be extended to the synthesis of oxindoles and an isoquinolinedione by the capturing of the sulfonyl radical with an alkene moiety. Moreover, the proposed mechanism was supported experimentally and by DFT calculations.
