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Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

Sofya I. Scherbinina, Oleg V. Fedorov, Vitalij V. Levin, Vladimir A. Kokorekin, Marina I. Struchkova and Alexander D. Dilman*

*N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Email:

S. I. Scherbinina, O. V. Fedorov, V. V. Levin, V. A. Kokorekin, M. I. Struchkova, A. D. Dilman, J. Org. Chem., 2017, 82, 12967-12974.

DOI: 10.1021/acs.joc.7b02467 (free Supporting Information)

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A photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate provides diversely substituted 3-fluoropyridines.

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proposed mechanism

Key Words

pyridines, photochemistry

ID: J42-Y2017