Nature Synthesis· 2026Q1
Scrambling-free synthesis of heteroleptic silylium ions by halide abstraction from halosilanes
- 1citations
- Q1SCImago
- 2026year
Short summary
A new method synthesizes heteroleptic silylium ions, which are highly reactive chemical intermediates, by abstracting halide from halosilanes without substituent scrambling.
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Key points
- Developed a method for synthesizing heteroleptic silylium ions, which are prone to substituent scrambling.
- Utilizes halosilanes as precursors and superhalophilic halogen-substituted silylium ions for halide abstraction.
- The reaction proceeds at ambient temperature without substituent redistribution.
- Enables access to diverse heteroleptic acyclic and cyclic silylium-ion motifs.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Heteroleptic silylium ions with different substituents at the silicon atom are generally not accessible using established tools for producing such reactive intermediates because substituent exchange reactions occur in acidic media, leading to homoleptic silylium ions with three identical alkyl and aryl substituents, respectively. Here we report a broadly applicable route to heteroleptic silylium ions using halosilanes as silylium ion precursors, which are less prone to that scrambling process. While this deceptively simple method has failed so far owing to the lack of a suitable halide-abstracting agent, superhalophilic halogen-substituted silylium ions enable smooth halide abstraction from a diverse set of halosilanes at ambient temperature without substituent redistribution. Accordingly, this approach provides access to essentially any heteroleptic acyclic as well as cyclic silylium-ion motif from common halosilanes, including trialkyl-, dialkyl(aryl)-, alkyldiaryl- and triaryl-substituted congeners. Computational calculations reveal the mechanism of heteroleptic silylium-ion formation and the origin of the suppressed substituent-scrambling process.
The authors' abstract, as published at the source. Nature Synthesis, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry