Multistep Synthesis of Organic Selenides under Visible Light Irradiation: A Continuous-Flow Approach,Organic Process Research & Development

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Multistep Synthesis of Organic Selenides under Visible Light Irradiation: A Continuous-Flow Approach
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2020-02-27 , DOI: 10.1021/acs.oprd.9b00548
Adrián A. Heredia ₁ , Silvia M. Soria-Castro ₁ , Willber D. Castro-Godoy ₂ , Ignacio D. Lemir ₁ , Martín López-Vidal ₁ , Fabricio R. Bisogno ₁ , Juan E. Argüello ₁ , Gabriela Oksdath-Mansilla ₁

Affiliation

The potential application of multistep continuous-flow systems has had a great impact on the syntheses of active pharmaceutical ingredients, natural products, and commodity chemicals. In this report, the highly efficient combination of a chemical reduction and a photochemical C_sp²–H activation reaction for selenylation of biologically relevant electron-rich arenes was achieved by means of a continuous-flow process. First, the reduction of alkyl and aryl selenocyanates by Rongalite was achieved giving the corresponding diselenides; second, the photoactivation of the Se–Se bond resulted in the selenylation of electron-rich arenes, both steps from good to excellent yields. In all cases, the reaction time was shortened, and isolated yields were improved when compared to batch reaction conditions. Furthermore, connecting both reactions in a multistep continuous-flow sequence was possible even when reductive and photooxidative transformations were coupled.

中文翻译：

可见光辐射下有机硒的多步合成：连续流方法

多步连续流系统的潜在应用对活性药物成分，天然产物和日用化学品的合成产生了巨大影响。在此报告中，化学还原和光化学C _sp_^2的高效组合用于生物相关的富电子芳烃的硒化反应的-H活化反应是通过连续流动过程实现的。首先，通过Rongalite还原了烷基和芳基硒氰酸酯，得到了相应的二硒化物。第二，Se-Se键的光活化导致富电子芳烃的硒化，这两个步骤都从良好的产率到优异的产率。在所有情况下，与间歇反应条件相比，反应时间都缩短了，分离的收率提高了。此外，即使在还原和光氧化转化相结合的情况下，以多步连续流顺序连接两个反应也是可能的。

更新日期：2020-02-27

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