PdH-Electrocatalytic Formal Conjugate Fluorination of β-Aryl-α,β-Unsaturated Amides with Mild and Safe Nucleophilic Fluorine Sources

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Abstract

An electrooxidative palladium-hydride catalytic system has been developed for the hydrofluorination of β-aryl-α,β-unsaturated amides using various nucleophilic fluorine sources, including Me4NF, Me4NF·tAmylOH, nBu4NF·(tBuOH)4, CsF, and KF. By avoiding hazardous HF-based reagents, this electrocatalytic protocol offers a safer and more practical route for the formal conjugate addition of fluoride to β-aryl-α,β-unsaturated amides, enabling access to β-fluoroamides. The method exhibits broad functional group tolerance, as exemplified by its application to the late-stage derivatization of complex molecules.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
StateAccepted/In press - 2025

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