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Updated: May 6, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Copper-Catalyzed Cascade Cross-Coupling/Cyclization of Silyl Enol Ethers for Synthesis of Polysubstituted Furans
Benxuan Gao1, Tongwei Liang1, Lucas M P Kusch2
1School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.
Abstract:
A novel protocol for a copper-catalyzed cascade cross-coupling/cyclization strategy utilizing silyl enolates has been developed, enabling the direct and highly regioselective construction of valuable 2,3,5-trisubstituted furans. Preliminary mechanistic investigations suggest that the reaction process involves a tandem carbon-carbon radical cross-coupling, formal 1,2-hydrogen migration, intramolecular Paal-Knorr cyclization, and aromatization. This protocol eliminates the necessity for initial 1,4-diketone preparation and demonstrates a broad substrate scope along with good functional group compatibility.
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