Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides

Fengjuan Chen, Youxiang Shao, Mengke Li, Can Yang, Shi-Jian Su (), Huanfeng Jiang, Zhuofeng Ke () and Wei Zeng ()
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Fengjuan Chen: South China University of Technology
Youxiang Shao: Sun Yat-sen University
Mengke Li: South China University of Technology
Can Yang: South China University of Technology
Shi-Jian Su: South China University of Technology
Huanfeng Jiang: South China University of Technology
Zhuofeng Ke: Sun Yat-sen University
Wei Zeng: South China University of Technology

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Sila-molecules have recently attracted attention due to their promising applications in medical and industrial fields. Compared with all-carbon parent compounds, the different covalent radius and electronegativity of silicon from carbon generally endow the corresponding sila-analogs with unique biological activity and physicochemical properties. Vinylsilanes feature both silyl-hyperconjugation effect and versatile reactivities, developing vinylsilane-based Smiles rearrangement will therefore provide an efficient platform to assemble complex silacycles. Here we report a practical Ir(III)-catalyzed cycloaromatization of ortho-alkynylaryl vinylsilanes with arylsulfonyl azides for delivering naphthyl-fused benzosiloles under visible-light photoredox conditions. The combination of experiments and density functional theory (DFT) energy profiles reveals the reaction mechanism involving α-silyl radical Smiles rearrangement.

Date: 2021
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DOI: 10.1038/s41467-021-23326-2

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