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Updated: May 28, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Nucleophilic Substitution at Unactivated Arene C-H: Copper-Catalyzed anti-Selective Silylative Cyclization of
Hirokazu Moniwa1, Ryo Shintani1,2
1Division of Chemistry, Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan.
Abstract:
A new mode of carbon-carbon bond formation via electrophilic activation of a C-H bond has been developed in the context of a copper-catalyzed anti-selective silylative cyclization of benzylacetylenes with silylboronates for the synthesis of 2-silyl-1H-indenes. The reaction proceeds with high regioselectivity for various substituted benzylacetylenes, and the resulting products could be further functionalized. The arene that undergoes cyclization acts as an electrophile with the release of hydride under redox neutral conditions, and the reaction mechanism was probed by the deuterium-labeling experiments and the density functional theory calculations.
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