Visible-Light-Induced α-C(sp3)–H Phosphinylation of Unactivated Ethers under Photocatalyst- and Additive-Free Conditions,The Journal of Organic Chemistry

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Visible-Light-Induced α-C(sp3)–H Phosphinylation of Unactivated Ethers under Photocatalyst- and Additive-Free Conditions
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-08-05 , DOI: 10.1021/acs.joc.2c01502
Bo Liu ₁ , Jianji Li ₁ , Yifan Hu ₁ , Qian Chen ₁ , Yan Liu ₁ , Shaomin Ji ₁ , Keiji Maruoka ₂ , Yanping Huo ₁ , Hao-Li Zhang _{1,

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Affiliation

A photocatalyst- and additive-free visible-light-induced α-C(sp³)–H phosphinylation of unactivated ethers involving a C–O bond cleavage with molecular oxygen as the sole oxidant at room temperature has been achieved. This method provides a sustainable access to α-hydroxyphosphine oxides in up to 88% yield with good functional group compatibility under mild and neutral conditions (34 examples). Moreover, the subsequent two-step conversion of the resulting dihydroxy diarylphosphine oxides afforded α-phosphinylated cyclic ethers in good overall yields (10 examples).

中文翻译：

在无光催化剂和无添加剂条件下，可见光诱导的 α-C(sp3)–H 未活化醚的膦酰化

已经实现了无光催化剂和无添加剂的可见光诱导的未活化醚的 α-C(sp ³ )-H 次膦酰化，其中涉及在室温下以分子氧作为唯一氧化剂的 C-O 键断裂。该方法可在温和和中性条件下以高达 88% 的收率持续获得 α-羟基膦氧化物，并具有良好的官能团相容性（34 个示例）。此外，所得二羟基二芳基氧化膦的后续两步转化以良好的总产率提供了 α-次膦酰化环醚（10 个实施例）。

更新日期：2022-08-05

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