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Organic Letters· 2026Q1

Room-Temperature C–C Bond Cleavage and Ring Expansion of Benzene by a Copper(I)-Substituted Silylene

Jiabao Chang, Cheng Xu, Yaofeng Chen

Short summary

A copper(I)-substituted silylene reversibly inserts into benzene C–C bonds at room temperature, enabling ring expansion and diverse functionalization via cleavage of the resulting Cu–Si bond.

AI-generated from the title and abstract; the full text is not read.

Key points

  • A copper(I)-substituted silylene cleaves benzene C–C bonds at room temperature.
  • The reaction forms a silepin intermediate with a Cu–Si bond.
  • The Cu–Si bond allows for diverse substitutions, including H, halogens, and various carbon-based groups.
  • This offers a mild method for benzene ring expansion and functionalization.

AI-generated from the title and abstract; the full text is not read.

Abstract

Abstract The cleavage and functionalization of benzene C–C bonds under mild conditions is of fundamental interest yet remains challenging. Herein, we report that an in situ generated copper(I)-substituted silylene undergoes reversible insertion into benzene at room temperature, affording a silepin with a reactive Cu–Si bond. This metal–silicon linkage enables diverse substitutions (H, halogen, alkyl, allyl, allenyl, propargyl) through facile cleavage, offering a mild strategy for benzene ring expansion and functionalization.

The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗

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Field: Inorganic Chemistry

Inorganic ChemistryChemistry