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Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives
Synthesis ( IF 2.2 ) Pub Date : 2021-10-26 , DOI: 10.1055/s-0040-1720921
Devaiah Vytla 1 , Kumargurubaran Kaliyaperumal 1 , Rajeswari Velayuthaperumal 1 , Parinita Shaw 1 , Raj Gautam 2 , Arvind Mathur 3 , Amrita Roy 1
Affiliation  

A photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF3SO2Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in good to excellent yields.

中文翻译:

N-芳基乙烯基磺酰胺的可见光促进自由基环化:合成含 CF3/CHF2/CH2CF3 的 1,3-二氢苯并[c]异噻唑 2,2-二氧化物衍生物

报道了在蓝光 LED 下使用市售的 CF3SO2Cl 作为三氟甲基自由基源对 N-芳基乙烯基磺酰胺进行光催化和高效三氟甲基化。该反应在温和条件下通过自由基环化进行。对底物范围进行了调查,以建立一个通用的、合成有用的协议,用于以中等至高产率合成新型三氟甲基化 1,3-二氢苯并 [c] 异噻唑 2,2-二氧化物。该方法还成功地用于合成二氟甲基化和三氟乙基化 1,3-二氢苯并[c]异噻唑 2,2-二氧化物,收率良好。
更新日期:2021-10-27
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