ArticleAngewandte Chemie (International ed. in English)2020
Silylium-Ion-Promoted (5+1) Cycloaddition of Aryl-Substituted Vinylcyclopropanes and Hydrosilanes Involving Aryl Migration.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- A Strong Lewis Acidic Diethylsilylium Catalyst for Direct Sulfonamidation of Challenging Ketones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Metal-Free Construction of Benzazepinoindoles in Water Enabled by an Ion-Pair Superacidic Precatalyst.Chemistry, an Asian journal · 2026Article
- SmIChemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Direct dehydrocoupling facilitates efficient thiophene anchoring on silicon surfaces.Nature communications · 2025Article
- The role of silicon in drug discovery: a review.RSC medicinal chemistry · 2024Review
- Access to Cyclic Borates by Cu-Catalyzed Borylation of Unactivated Vinylcyclopropanes.Organic letters · 2024Article
- NHC-Ni(II)-catalyzed cyclopropene-isocyanide [5 + 1] benzannulation.Nature communications · 2022Article
- Intermolecular Carbosilylation of α-Olefins with C(spAngewandte Chemie (International ed. in English) · 2022Article
- Synthesis of 1-Silabenzo[ACS omega · 2022Article
- Metal-Free Hydrosilylation of Ketenes with Silicon Electrophiles: Access to Fully Substituted Aldehyde-Derived Silyl Enol Ethers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Intramolecular Friedel-Crafts alkylation with a silylium-ion-activated cyclopropyl group: formation of tricyclic ring systems from benzyl-substituted vinylcyclopropanes and hydrosilanes.Chemical science · 2020Article
- Silylium-Ion-Promoted (5+1) Cycloaddition of Aryl-Substituted Vinylcyclopropanes and Hydrosilanes Involving Aryl Migration.Angewandte Chemie (International ed. in English) · 2020Article
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5 authors.
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Abstract
A transition-metal-free (5+1) cycloaddition of aryl-substituted vinylcyclopropanes (VCPs) and hydrosilanes to afford silacyclohexanes is reported. Catalytic amounts of the trityl cation initiate the reaction by hydride abstraction from the hydrosilane, and further progress of the reaction is maintained by self-regeneration of the silylium ions. The new reaction involves a [1,2] migration of an aryl group, eventually furnishing 4- rather than 3-aryl-substituted silacyclohexane derivatives as major products. Various control experiments and quantum-chemical calculations support a mechanistic picture where a silylium ion intramolecularly stabilized by a cyclopropane ring can either undergo a kinetically favored concerted [1,2] aryl migration/ring expansion or engage in a cyclopropane-to-cyclopropane rearrangement.
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