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Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides.

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.

SUBMITTER: Chen F

PROVIDER: S-EPMC8175346 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides.

Chen Fengjuan F Shao Youxiang Y Li Mengke M Yang Can C Su Shi-Jian SJ Jiang Huanfeng H Ke Zhuofeng Z Zeng Wei W

Nature communications 20210603 1

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 pro ...[more]

PMID: 34083532

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