Defluorophosphorylation of fluoroalkyl peroxides for the synthesis of highly substituted furans
Defluorophosphorylation of fluoroalkyl peroxides for the synthesis of highly substituted furans
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合成高取代呋喃的氟烷基过氧化物的去氟磷酸化反应
DOI：
10.1039/d2gc04512e
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发表时间：
2023-02-08
期刊：
影响因子：
9.8
通讯作者：
Shen, Zhi-Liang
中科院分区：
文献类型：
--
作者：
Chu, Xue-Qiang;Cai, Song-Zhou;Shen, Zhi-Liang
通过控制选址选择性和化学多样性来改造多功能材料仍然具有挑战性。在此，我们提出了一种不含金属的一锅法策略，用于多氟烷基过氧化物的脱氟磷酸化，从而能够方便地构建结构多样的含磷杂环库。通过合理选择反应条件，可以容易地获得C3，4-二磷酰基呋喃和C4-单磷酰基呋喃。此外，合成衍生得到的有机磷杂芳烃增值单齿和双齿膦已被证明。机理研究表明，区域选择性脱氟磷酸化允许不同的产品形成两种反应模式。
Transformation of multifunctional materials with control over site-selectivity and chemical diversity remains challenging. Herein, we present a metal-free, one-pot strategy for the defluorophosphorylation of polyfluoroalkyl peroxides that enables expedient construction of structurally diverse phosphoryl-containing heterocyclic libraries. By judicious choice of reaction conditions, C3,4-diphosphoryl furans and C4-monophosphoryl furans can be easily accessed. In addition, synthetic derivatization of the obtained organophosphorus heteroarenes to value-added monodentate and bidentate phosphines has been demonstrated. Mechanistic studies revealed that regioselective defluorophosphorylation allows divergent product formation in two reaction modes.