Zhang Kuan, Gao Zhengyang, Xia Yan, Li Pengfei, Gao Pin, Duan Xin-Hua, Guo Li-Na
Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University Xi'an 710049 China
Frontier Institute of Science and Technology, State Key Laboratory for Mechanical Behavior of Materials, Xi'an Jiaotong University Xi'an 710049 China.
Chem Sci. 2024 Dec 13;16(3):1411-1416. doi: 10.1039/d4sc07243j. eCollection 2025 Jan 15.
Although bicyclo[4.1.1] systems are privileged scaffolds in many natural products and drug molecules, efficient synthetic approaches to these systems remain underdeveloped. In this work, we disclose a photoredox-catalyzed defluorinative (4 + 3) annulation of bicyclo[1.1.0]butanes with -difluoroalkenes, which provides practical and straightforward access to the fluorine-containing bicyclo[4.1.1]octenes. Our protocol is characterized by mild conditions, broad substrate scope, excellent functional group tolerance and good to excellent yields. Notably, the ease and variety of product derivatizations further enrich the diversity and complexity of the fluorine-containing bicyclo[4.1.1] systems.
尽管双环[4.1.1]体系在许多天然产物和药物分子中是具有优势的骨架，但针对这些体系的高效合成方法仍未得到充分发展。在这项工作中，我们报道了一种光氧化还原催化的双环[1.1.0]丁烷与二氟烯烃的脱氟（4 + 3）环化反应，该反应为含氟双环[4.1.1]辛烯提供了实用且直接的合成途径。我们的方法具有条件温和、底物范围广、官能团耐受性优异以及产率良好至优异的特点。值得注意的是，产物衍生化的简便性和多样性进一步丰富了含氟双环[4.1.1]体系的多样性和复杂性。
