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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Palladium-catalyzed defluorinative coupling of indoles with α,α-difluoro-β,γ-unsaturated ketones: direct access to
Chunming Chen1, Huixuan Zhu1, Zhenli Luo1
1School of Pharmacy and Food Engineering, Wuyi University, No. 99 Yingbin Road, Jiangmen 529020, China. wyuchemwjq@wyu.edu.cn.
Abstract:
A palladium-catalyzed defluorinative coupling of indoles with α,α-difluoro-β,γ-unsaturated ketones is reported. This method provides direct access to a diverse range of functionalized (Z)-α-fluoroenones in moderate to excellent yields under mild conditions. The reaction exhibits broad substrate scope and functional group tolerance for both coupling partners, including electron-rich, electron-deficient, and sterically hindered indoles, as well as aryl, heteroaryl, and alkyl-substituted fluorinated ketones. It is operationally simple, scalable, and proceeds under ambient atmosphere.
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