Iron‐Mediated Cyanoalkylsulfonylation/Arylation of Active Alkenes with Cycloketone Oxime Derivatives via Sulfur Dioxide Insertion,Advanced Synthesis & Catalysis

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Iron‐Mediated Cyanoalkylsulfonylation/Arylation of Active Alkenes with Cycloketone Oxime Derivatives via Sulfur Dioxide Insertion
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-05-14 , DOI: 10.1002/adsc.202000369
Zan Chen ₁ , Quan Zhou ₁ , Qiao‐Lin Wang ₁ , Pu Chen ₁ , Bi‐Quan Xiong ₁ , Yun Liang ₂ , Ke‐Wen Tang ₁ , Yu Liu _{1,

2}

Affiliation

Iron‐mediated radical cyanoalkylsulfonylation/arylation of active olefins with cycloketone oxime derivatives via cleavage of C−C single bond and insertion of SO₂ is developed for the preparation of cyanoalkylsulfonylated oxindoles. This difunctionalization of carbon−carbon double bond via a radical pathway involves cyclobutanone oxime ester fragmentation, sulfonyl radical generation and radical addition/5‐exo cyclization. The methodology displays good functional group tolerance and does not require any external bases or oxidants.

中文翻译：

铁介导的氰基烷基磺酰基化/活性烯烃与环酮肟衍生物的二氧化硫插入化

开发了通过裂解C-C单键和插入SO _2的铁介导的自由基与环酮肟衍生物的活性烯烃氰基烷基磺酰化/芳基化反应，用于氰基烷基磺酰化的吲哚的制备。碳-碳双键通过自由基途径的双官能团化涉及环丁酮肟酯的断裂，磺酰基自由基的产生和自由基加成/ 5-外型环化。该方法显示出良好的官能团耐受性，不需要任何外部碱或氧化剂。

更新日期：2020-05-14

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