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Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

Sungwoo Jung, Sanghoon Shin, Seongjin Park and Sungwoo Hong*

*Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Korea, Email:

S. Jung, S. Shin, S. Park, S. Hong, J. Am. Chem. Soc., 2020, 142, 11370-11375.

DOI: 10.1021/jacs.0c04499 (free Supporting Information)


A photochemical cross-coupling between N-amidopyridinium salts and various alkyl bromides under photocatalyst-free conditions provides various C4-alkylated pyridines. The photochemical activity of electron donor-acceptor (EDA) complexes between N-amidopyridinium salts and bromide generates silyl radicals and drives the alkylation process.

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Key Words

pyridines, tris(trimethylsilyl)silane, photochemistry

ID: J48-Y2020