Photoexcited Palladium-Initiated Remote Desaturation of <i>N</i>-Alkoxypyridinium Salts

Abstract

1,5-Hydrogen atom transfer (HAT) is an effective strategy to achieve remote desaturation of nonfunctionalized alkanes. Herein, we report a photoinduced remote desaturation reaction of N-alkoxypyridinium salts, which serve as alkoxyl radical precursors. Mechanistic studies show that a single electron transfer between the excited palladium complex and a N-alkoxypyridinium salt initiates a radical chain process leading to desaturation of N-alkoxypyridinium salts. This chain mechanism is supported by the measurement of the quantum yield of this reaction (Φ = 82). This reaction is applicable to a range of N-alkoxypyridinium salts, including some complex molecule-derived ones.

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