ArticleAngewandte Chemie (International ed. in English)2019
Catalytic Difunctionalization of Unactivated Alkenes with Unreactive Hexamethyldisilane through Regeneration of Silylium Ions.
Article in Angewandte Chemie (International ed. in English), 2019. 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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Who cites it
7 citing papers in PubMed.
- Silylium-Ion-Initiated Disulfidation of Internal Alkynes With Disulfides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Photocatalytic 1,3-difluoroalkylcarboxylation of alkenes by triple kinetic-controlled radical self-ordering.Chemical science · 2025Article
- Bis-silylation of internal alkynes enabled by Ni(0) catalysis.Nature communications · 2021Article
- An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond.Journal of the American Chemical Society · 2020Article
- 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
- Catalytic Difunctionalization of Unactivated Alkenes with Unreactive Hexamethyldisilane through Regeneration of Silylium Ions.Angewandte Chemie (International ed. in English) · 2019Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
A metal-free, intermolecular syn-addition of hexamethyldisilane across simple alkenes is reported. The catalytic cycle is initiated and propagated by the transfer of a methyl group from the disilane to a silylium-ion-like intermediate, corresponding to the (re)generation of the silylium-ion catalyst. The key feature of the reaction sequence is the cleavage of the Si-Si bond in a 1,3-silyl shift from silicon to carbon. A central intermediate of the catalysis was structurally characterized by X-ray diffraction, and the computed reaction mechanism is fully consistent with the experimental findings.
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