Xia Xi-Rui, Du Juan, Zhang Yu-Xing, Jiang Hong, Cheng Wan-Min
College of Chemistry, Huazhong Agricultural University, Wuhan, 430070, China.
ChemSusChem. 2024 Nov 25;17(22):e202400650. doi: 10.1002/cssc.202400650. Epub 2024 Aug 8.
A convenient and sustainable method for synthesizing sulfonyl-containing compounds through a catalyst-free aqueous-phase hydrosulfonylation of alkenes and alkynes with sulfonyl chlorides under visible light irradiation is presented. Unactivated alkenes, electron-deficient alkenes, alkyl and aryl alkynes can be hydrosulfonylated with various sulfonyl chlorides at room temperature with excellent yields and geometric selectivities by using tris(trimethylsilyl)silane as a hydrogen atom donor and silyl radical precursor to activate sulfonyl chlorides. Mechanistic studies revealed that the photolysis of tris(trimethylsilyl)silane in aqueous solution to produce silyl radical is crucial for the success of this reaction.
本文提出了一种便捷且可持续的方法，即在可见光照射下，通过烯烃和炔烃与磺酰氯的无催化剂水相氢磺酰化反应来合成含磺酰基的化合物。通过使用三（三甲基硅基）硅烷作为氢原子供体和硅基自由基前体来活化磺酰氯，未活化的烯烃、缺电子烯烃、烷基和芳基炔烃能够在室温下与各种磺酰氯进行氢磺酰化反应，产率优异且具有几何选择性。机理研究表明，三（三甲基硅基）硅烷在水溶液中的光解以产生硅基自由基对于该反应的成功至关重要。
