Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations,Angewandte Chemie International Edition

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Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-10-15 , DOI: 10.1002/anie.202010437
Hao Liang ₁ , Lu‐Jun Wang ₁ , Yun‐Xing Ji ₁ , Han Wang ₁ , Bo Zhang ₁

Affiliation

The first electrochemical hydrolysis of hydrosilanes to silanols under mild and neutral reaction conditions is reported. The practical protocol employs commercially available and cheap NHPI as a hydrogen‐atom transfer (HAT) mediator and operates at room temperature with high selectivity, leading to various valuable silanols in moderate to good yields. Notably, this electrochemical method exhibits a broad substrate scope and high functional‐group compatibility, and it is applicable to late‐stage functionalization of complex molecules. Preliminary mechanistic studies suggest that the reaction appears to proceed through a nucleophilic substitution reaction of an electrogenerated silyl cation with H₂O.

中文翻译：

硅烷通过阳极生成的甲硅烷基阳离子选择性水解为硅烷醇

据报道，在温和和中性的反应条件下，氢化硅烷首次电化学水解为硅烷醇。该实用方案使用可商购的廉价NHPI作为氢原子转移（HAT）介体，并在室温下以高选择性运行，从而以中等至良好的收率生产出各种有价值的硅烷醇。值得注意的是，这种电化学方法具有广泛的底物范围和较高的官能团相容性，适用于复杂分子的后期官能化。初步的机理研究表明，该反应似乎是通过电产生的甲硅烷基阳离子与H ₂ O的亲核取代反应进行的。

更新日期：2020-10-15

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