ArticleNature communications2021
Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
7 citing papers in PubMed.
- Smiles-Truce Cascades Enable Heteroaryl Cyclopropane and Sultine Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Aryne-Enabled C-N Arylation of Anilines.Angewandte Chemie (International ed. in English) · 2023Article
- An NHC-Catalyzed Desulfonylative Smiles Rearrangement of Pyrrole and Indole Carboxaldehydes.The Journal of organic chemistry · 2023Article
- Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols.Nature communications · 2023Article
- Synthetic strategies to access silacycles.Frontiers in chemistry · 2023Review
- Copper-catalyzed cross coupling reaction of sulfonyl hydrazides with 3-aminoindazoles.RSC advances · 2022Article
- Diarylamine Synthesis via Desulfinylative Smiles Rearrangement.Organic letters · 2022Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
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.
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Registered trials
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