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

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journal contribution
posted on 18.06.2020, 16:09 by Sungwoo Jung, Sanghoon Shin, Seongjin Park, Sungwoo Hong
Reported herein is a general strategy for the photochemical cross-coupling between N-amido­pyridinium salts and various alkyl bromides under photocatalyst-free conditions, granting facile access to various C4-alkylated pyridines. This approach exploits the intriguing photochemical activity of electron donor–acceptor (EDA) complexes between N-amido­pyridinium salts and bromide, which provides a photoactive handle capable of generating silyl radicals and driving the alkylation process. The robustness of this protocol was further demonstrated by the late-stage functionalization of complex compounds under mild and metal-free conditions.