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·2025
C4-Selective Alkylation of Pyridines through Amidyl-Radical-Mediated 1,2-Hydrogen Atom Transfer
Sungwoo Hong, H. L. Ju, Chang‐Yin Tan
IF 1.4Synlett
초록

Abstract Hydrogen atom transfer (HAT) reactions play a vital role in radical chemistry and biological systems, enabling selective C–H functionalization through bond dissociation energy and polarity effects. Whereas intramolecular 1,5-HAT is well established, 1,2-HAT processes remain relatively challenging, particularly for nitrogen-centered radicals, due to high activation barriers. Here, we report a successful 1,2-HAT of amidyl radicals generated from N-amidopyridinium salts, enabled by a frustrated Lewis pair system of t-Bu3P and the pyridinium salt, without requiring an external photocatalyst. The phosphine serves dual roles: reducing the pyridinium salt through single-electron transfer and facilitating the 1,2-HAT process under mild conditions. Visible-light irradiation enhances the reaction efficiency, allowing late-stage functionalization of pyridine-containing pharmaceuticals. This method offers a new approach to selective pyridine C–H functionalization, broadening the scope of HAT chemistry in synthesis.

키워드
ChemistryAlkylationHydrogen atomHydrogenPhotochemistryOrganic chemistryCombinatorial chemistryCatalysisGroup (periodic table)
타입
article
IF / 인용수
1.4 / 0
게재 연도
2025

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