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Updated: Apr 6, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Palladium-Catalyzed Oxidative Cross-Coupling of Conjugated Enynones with Organoboronic Acids
1†Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Abstract:
A palladium-catalyzed oxidative cross-coupling reaction of conjugated enynones with organoboronic acids is developed. This reaction provides an efficient methodology for the synthesis of functionalized furan derivatives, including 2-alkenylfurans and furan-substituted 1,3-dienes. Palladium-carbene migratory insertion is proposed as the key step in these transformations. Notably, the β-hydride elimination process occurs in a stereoselective manner, resulting in the formation of double bonds with high (E)-selectivity.
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