Visible-light-induced direct perfluoroalkylation/heteroarylation of [1.1.1]propellane to diverse bicyclo[1.1.1]pentanes (BCPs) under metal and photocatalyst-free conditions,Green Chemistry

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Visible-light-induced direct perfluoroalkylation/heteroarylation of [1.1.1]propellane to diverse bicyclo[1.1.1]pentanes (BCPs) under metal and photocatalyst-free conditions
Green Chemistry ( IF 9.3 ) Pub Date : 2023-01-12 , DOI: 10.1039/d2gc04521d
Jiashun Zhu ₁ , Yirui Guo ₁ , Yuru Zhang ₁ , Wanmei Li ₁ , Pengfei Zhang ₁ , Jun Xu ₁

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Herein, a green and novel multi-component reaction for direct perfluoroalkylation/heteroarylation of [1.1.1]propellane with heteroarenes and perfluoroalkyl iodines has been described. This transformation is facilitated by visible light in the absence of any transition-metal catalysts and photocatalysts. Various heteroarenes and perfluoroalkyl iodines are well compatible, providing the corresponding products in moderate-to-good yields. The control experiments demonstrate that a radical-relay mechanism is responsible for the cascade reaction. Such a methodology offers an efficient and practical access to diverse 1-perfluoroalkyl-3-heteroaryl bicyclo[1.1.1]pentanes (BCPs) with the potential for various applications in organic synthesis.

中文翻译：

在无金属和无光催化剂的条件下，可见光诱导的 [1.1.1] 丙烷直接全氟烷基化/杂芳基化为多种双环 [1.1.1] 戊烷 (BCP)

在此，描述了 [1.1.1] 丙烷与杂芳烃和全氟烷基碘的直接全氟烷基化/杂芳基化的绿色新型多组分反应。在没有任何过渡金属催化剂和光催化剂的情况下，可见光促进了这种转化。各种杂芳烃和全氟烷基碘具有很好的相容性，以中等到良好的收率提供相应的产品。控制实验表明自由基中继机制负责级联反应。这种方法提供了一种有效且实用的方法来获得各种 1-perfluoroalkyl-3-heteroaryl 双环 [1.1.1] 戊烷 (BCP)，并具有在有机合成中的各种应用潜力。

更新日期：2023-01-12

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