Diversity-Oriented Synthesis of Flavones and Isoflavones via Palladium/Norbornene Cooperative Catalysis
Diversity-Oriented Synthesis of Flavones and Isoflavones via Palladium/Norbornene Cooperative Catalysis
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钯/降冰片烯协同催化多样性合成黄酮和异黄酮
DOI：
10.1002/cjoc.202100693
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Zhou Qianghui
中科院分区：
文献类型：
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作者：
Ma Yuanyuan;Gao Qianwen;Zhou Lan;Liu Shanshan;Cheng Hong-Gang;Zhou Qianghui
黄酮类和异黄酮类化合物被公认为是制备生物活性化合物的优良杂环支架。迫切需要有效的方法来获取这些杂环。在这里，我们报道了在钯/降冰片烯协同催化下，以3-碘色酮为原料，以多样性为目标的黄酮类和异黄酮类化合物的合成。这项研究的成功依赖于使用一种独特的桥头酯修饰的降冰片烯衍生物作为介体。它的显著特点包括：3-碘色酮、邻位C-H芳基化试剂和烷基化试剂的起始原料容易获得，底物范围广，良好的化学选择性，良好的步骤经济性和可扩展性。可以以可预测的方式快速制备大量结构多样化的黄酮类、异黄酮类和2，3-二芳基色酮。正如有效的形式合成umbralisib所显示的那样，这种化学可以被视为药物化学家工具箱中的又一有价值的补充。
Comprehensive SummaryFlavones and isoflavones are recognized as privileged heterocyclic scaffolds for the preparation of bioactive compounds. Efficient methods to access these heterocycles are in urgent need. Herein, we report diversity‐oriented synthesis of flavones and isoflavones from 3‐iodochromones via palladium/norbornene cooperative catalysis. The success of this research relies on the use of a unique bridge‐head ester modified norbornene derivative as the mediator. Salient features of this include readily available starting materials regarding 3‐iodochromones,ortho‐C—H arylating and alkylating reagents andipso‐terminating reagents, broad substrate scope, good chemoselectivity, good step‐economy and scalability. A large number of structurally diversified flavones, isoflavones and 2,3‐diarylated chromones can be quickly prepared in a predictable manner. As showcased by the efficient formal synthesis of umbralisib, this chemistry can be treated as another valuable addition to the toolbox of medicinal chemists.