A Palladium-Catalyzed Borylation/Silica Gel Promoted Hydrolysis Sequence for the Synthesis of Hydroquinine-6′-Boric Acid and Its Applications
A Palladium-Catalyzed Borylation/Silica Gel Promoted Hydrolysis Sequence for the Synthesis of Hydroquinine-6′-Boric Acid and Its Applications
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DOI：
10.1021/acs.joc.3c00774
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发表时间：
2023-07-20
影响因子：
3.6
通讯作者：
Chen, Lin
中科院分区：
文献类型：
--
作者：
Liang, Wei;Chen, Zheng-Jun;Chen, Lin
首先通过钯催化的硼酸化/硅胶促进氢奎宁衍生的三氟甲磺酸酯和双(频那醇)二硼的水解序列合成了氢奎宁-6 & PRIME;-硼酸。新设计的手性结构单元分别进行了 Suzuki-Miyauracross 偶联反应、Petasis 反应和硒化反应，所有这些反应均运行良好，得到了相应的 6 & PRIME;-硼酸。 PRIME;-功能化氢奎宁效果令人满意，展示了其非凡的应用潜力。
Hydroquinine-6 & PRIME;-boric acid was first synthesized via a palladium-catalyzed borylation/silica gel promotedhydrolysis sequence of hydroquinine-derived triflate and bis(pinacolato)diboron.The newly designed chiral building block was subjected to the Suzuki-Miyauracross-coupling reaction, Petasis reaction, and selenylation reaction,respectively, and all these reactions worked well to afford the corresponding6 & PRIME;-functionalized hydroquinines with satisfactory results,demonstrating its extraordinary application potency.