Site-Selective Synthesis of N‑Benzyl 2,4,6-Collidinium Salts by Electrooxidative C–H Functionalization

N-alkylpyridinium salts are versatile pseudohalides for SET-mediated cross couplings. However, the common 2,4,6-triphenylpyridinium salt is plagued by poor atom economy and high cost of synthesis. Thus, there is a growing need for more practical scaffolds and innovative strategies for pyridinium sal...

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Bibliographic Details
Published in:Organic letters 2022-08, Vol.24 (32), p.6060-6065
Main Authors: Motsch, Bill J., Wengryniuk, Sarah E.
Format: Article
Language:English
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Summary:N-alkylpyridinium salts are versatile pseudohalides for SET-mediated cross couplings. However, the common 2,4,6-triphenylpyridinium salt is plagued by poor atom economy and high cost of synthesis. Thus, there is a growing need for more practical scaffolds and innovative strategies for pyridinium salt formation. Herein, we report the synthesis of benzylic 2,4,6-collidinium salts via electrooxidative C–H functionalization. This method provides a complementary approach to tradtional strategies relying on substitution and condensation of prefunctionalized substrates.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02376