Photocatalytic Generation of β-Fluoroalkylated α-Carbonyl Carbocations

Chong Jin Zhang, Zhen Zhen Liu, Yan Biao Kang, Jian Ping Qu

Research output: Contribution to journalArticlepeer-review

Abstract

Nucleophilic addition to α,β-unsaturated carbonyl compounds normally occurs at the carbonyl carbon or β-carbon. The direct α-nucleophilic addition at the α-carbon can hardly be achieved due to electronic mismatch. In this work, we report the nucleophilic addition of β-fluoroalkyl α-carbonyl carbocations that are prepared via CBZ6-induced redox-neutral photocatalysis. In this process, the photocatalytic oxidation of the β-fluoroalkyl α-carbonyl radical to the corresponding carbocation is the key step. The β-fluoroalkyl α-carbonyl radical is generated in situ by the addition of a polyfluoroalkyl radical, which is generated by the photocatalytic fragmentation of polyfluoroalkyl sulfonyl chloride, to α,β-unsaturated carbonyls. The high E00 value of CBZ6 (3.19 V vs the saturated calomel electrode), which corresponds with the absorbed photoenergy, contributes to the high catalytic reactivity.

Original languageEnglish
Pages (from-to)264-268
Number of pages5
JournalOrganic Letters
Volume27
Issue number1
DOIs
StatePublished - 10 Jan 2025

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