Electrochemically Induced Regio- and Stereoselective (E)-β-C(sp2)−H Trifluoromethylation and Arylsulfonylation of Enamides,Advanced Synthesis & Catalysis

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Electrochemically Induced Regio- and Stereoselective (E)-β-C(sp2)−H Trifluoromethylation and Arylsulfonylation of Enamides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-01 , DOI: 10.1002/adsc.202200934
Fukuan Zhang ₁ , Xuefei Zhao ₂ , Jie Zhang ₁ , Lili Zhao ₂ , Lin Li ₁ , Jiayi Yang ₁ , Hao Li ₁ , Haiqing Luo ₁

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Herein, we disclosed an electrochemically induced method for the regio- and stereoselective (E)-β-C(sp²)−H trifluoromethylation of enamides by employing readily available and inexpensive Langlois’ reagent (CF₃SO₂Na). Preliminary mechanistic studies indicate the involvement of free radicals in the process. The exogenous oxidant-free reaction proceeds in an undivided electrochemical cell under mild conditions and allows for the accomplishment of the trifluoromethylation products with exclusive E-selective control. The methodology is featured by catalyst-free, simple setup, and broad substrate scopes of enamides with good functional group tolerance. Using ArSO₂Na as the coupling partner, the corresponding (E)-β-C(sp²)−H arylsulfonylated enamides products are obtained under standard reaction conditions.

中文翻译：

电化学诱导的区域选择性和立体选择性 (E)-β-C(sp2)−H 三氟甲基化和烯酰胺的芳基磺酰化

在此，我们公开了一种电化学诱导的区域选择性和立体选择性 ( E )-β-C( sp ² )-H 三氟甲基化的方法，使用现成且廉价的 Langlois 试剂 (CF ₃ SO ₂ Na)。初步的机理研究表明自由基参与了这个过程。无外源氧化剂的反应在温和条件下在未分隔的电化学电池中进行，并允许通过独家E选择性控制完成三氟甲基化产物。该方法的特点是无催化剂、设置简单、烯酰胺底物范围广、官能团耐受性好。使用 ArSO ₂Na 作为偶联配偶体，在标准反应条件下得到相应的 ( E )-β-C( sp ² )−H 芳基磺酰化烯酰胺产物。

更新日期：2022-11-01

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