Visible-light-induced aerobic C-3 thiocyanation of indoles using porphyrin as photoredox catalyst

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-04-18 DOI:10.1080/00397911.2025.2477650

Pritesh P. Khobrekar (Conceptualization Data curation Formal analysis Methodology Writing – original draft Writing – review & editing) , Pooja V. Shreechippa (Formal analysis) , Rutika R. Gawas (Formal analysis) , Ratan W. Jadhav (Formal analysis) , Vishnu R. Chari (Software) , Sheshanath V. Bhosale (Conceptualization Project administration Supervision Writing – review & editing) , Sandesh T. Bugde (Conceptualization Investigation Project administration Supervision Validation Writing – review & editing)

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引用次数: 0

Abstract

In this work, we report a metal-free and environmentally friendly approach for the electrophilic C–H thiocyanation of indoles under visible light irradiation. Using porphyrin as a photocatalyst and atmospheric air as an oxidant, we developed a mild and efficient route to synthesize a series of thiocyanate products with both electron-rich and electron-deficient systems in moderate to good yields. The use of a radical scavenger like TEMPO helped to establish a photoredox mechanism. This method offers a sustainable and promising approach for synthesizing heterocyclic substrates, thiocyanate aromatics, and bioactive molecules through photoredox catalysis.

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卟啉作为光氧化还原催化剂的可见光诱导吲哚的C-3好氧硫氰化反应

在这项工作中，我们报告了一种在可见光照射下进行吲哚亲电C-H硫氰化的无金属和环境友好的方法。以卟啉为光催化剂，以大气为氧化剂，研究了一种温和高效的合成富电子和缺电子硫氰酸盐系列产品的方法。使用像TEMPO这样的自由基清除剂有助于建立光氧化还原机制。该方法为通过光氧化还原催化合成杂环底物、硫氰酸酯芳烃和生物活性分子提供了一种可持续的、有前途的方法。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.