河北农业大学张金林/张越OL:可见光驱动光氧化还原/HAT共催化策略助力α‑三氟甲基烯烃的C-F键官能团化反应合成偕二氟烯丙基有机锗化合物

图1. TOC (图片来源于Org. Lett.)

摘要：

This study describes a visible-light-driven photoredox/HAT cocatalytic strategy for the efficient synthesis of functionalized 3,3-difluoroallyl organogermanium compounds. Bioactivity studies indicate that representative compound 3q exhibits significant herbicidal activity against Portulaca oleracea L. with an inhibition rate of 72.6%, comparable to the commercial herbicide atrazine. Integrating continuous-flow technology enabled gram-scale synthesis. This work provides an approach to fluorinated organogermanium compounds and may facilitate the development of agrochemical agents.

研究背景：

图2. 具有生物活性的二氟烯烃骨架 (图片来源于Org. Lett.)

图3. 研究背景及本策略 (图片来源于Org. Lett.)

研究内容：

图4. 条件优化 (图片来源于Org. Lett.)

图5. 底物拓展 (图片来源于Org. Lett.)

图6. 生物活性和理论研究 (图片来源于Org. Lett.)

图7. 连续流动光化学实现克级合成反应 (图片来源于Org. Lett.)

图8. 可能的反应机理 (图片来源于Org. Lett.)

总结：

In summary, we have developed a sustainable catalytic platform for the construction of gem-difluoroallyl organogermanium compounds. This method employs photoredox/HAT cocatalysis, enabling selective C−F bond cleavage and C−Ge bond formation under mild conditions. The protocol exhibits broad substrate scope and is compatible with structurally complex natural products and agrochemical derivatives. Notably, the herbicidal activities of the target compounds were systematically evaluated, revealing that compound 3q exhibits excellent activity against P. oleracea. Preliminary studies, including mechanism of action analysis and ADMET prediction, further suggest its application potential. Furthermore, gram-scale synthesis of this reaction system was accomplished under continuous-flow conditions, demonstrating its practical utility and scalability. This work provides a versatile and sustainable strategy for the synthesis of fluorinated organogermanium compounds and offers guidance for the development of herbicides.

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