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Updated: Jun 3, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Hydroxyalkylation of α-Silylamines via a Photoredox Polarity-Matched Strategy
Zhonghua Qu1, Shuai Wang1, Zhihong He1
1Department of Chemistry, School of Science, Xihua University, Chengdu 610039, China.
Abstract:
A step-economic, photoredox-catalyzed hydroxyalkylation of nucleophilic α-silylamines with diverse electrophilic carbonyls to access biologically relevant β-amino alcohols. In contrast to the classical multistep Henry reaction, this one-step approach utilizes a polarity-matched strategy to directly forge the target scaffolds. This protocol features remarkable substrate/functional group compatibility, scale-up potential, and facile late-stage modification. Mechanistic studies reveal the formation of the α-amino radical from α-silylamines by a single-electron oxidative desilylation.
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