Integrating Continuous-Flow Electrochemistry and Photochemistry for the Synthesis of Acridinium Photocatalysts Via Site-Selective C–H Alkylation,Organic Process Research & Development

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Integrating Continuous-Flow Electrochemistry and Photochemistry for the Synthesis of Acridinium Photocatalysts Via Site-Selective C–H Alkylation
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2021-03-05 , DOI: 10.1021/acs.oprd.1c00038
Hong Yan ₁ , Shaobin Zhu ₂ , Hai-Chao Xu ₁

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Acridinium dyes are among the most frequently studied classes of organic photocatalysts because of their favorable excited-state properties such as high reduction potential and good lifetime. However, it remains challenging to modulate their catalytic performance by a structural modification. Here, we report a two-step continuous-flow system for the synthesis of functionalized acridinium photocatalysts through a site-selective late-stage C(aryl)–H functionalization of the acridinium core. The alkylation is achieved by pumping the parent acridinium dye sequentially through a photoreactor to achieve cross-coupling with an organotrifluoroborate and an electrochemical reactor for electrocatalytic dehydrogenation. The two-step automatic system allows the introduction of a diverse range of alkyl groups at the 3-position of the acridinium dye. Subjecting 3-alkylated acridinium salts to the flow system for a second alkylation forms 3,6-disubstituted acridinium dyes.

中文翻译：

集成连续流动电化学和光化学通过位点选择性 C-H 烷基化合成吖啶光催化剂

吖啶染料是最常研究的有机光催化剂类别之一，因为它们具有良好的激发态特性，例如高还原电位和良好的寿命。然而，通过结构修饰来调节其催化性能仍然具有挑战性。在这里，我们报告了一个两步连续流动系统，用于通过吖啶核的位点选择性后期 C(芳基)-H 功能化合成功能化吖啶光催化剂。烷基化是通过将母体吖啶染料依次泵送通过光反应器以实现与有机三氟硼酸盐和电化学反应器的交叉偶联实现电催化脱氢。两步自动系统允许在吖啶染料的 3 位引入不同范围的烷基。

更新日期：2021-03-05

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