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Updated: Apr 8, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Progress in intermolecular radical umpolung addition to alkenes
Yeming Wang1,2, Chaoqun Zhang1,2, Jian-Quan Liu3
1Institute of Chemical and Industrial Bioengineering, Jilin Engineering Normal University, Changchun, Jilin, 130052, China. wangyeming2019@163.com.
Abstract:
Conventional organic synthesis is constrained by innate polarity, often requiring multi-step sequences under harsh conditions. The "umpolung" strategy enables polarity reversal for unconventional bond formations, while radical chemistry efficiently forges C-C bonds under mild conditions. Integration of radical chemistry with umpolung tactics has rapidly evolved into a versatile paradigm, significantly expanding the synthetic toolbox. This review summarizes recent advances in the intermolecular umpolung radical (α-carbonyl, α-sulfonyl, and acyl radicals) addition to alkenes, focusing on radical generation, alkene addition, functionalization pathways, and mechanistic insights that enable efficient access to architecturally diverse molecules.
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