C4-Selective C–H Borylation of Pyridinium Derivatives Driven by Electron Donor–Acceptor Complexes

The photoinduced C4-selective C–H borylation of pyridines was achieved using electron donor–acceptor complexes derived from a Lewis base and N-amidopyridinium salts under external oxidant- and photocatalyst-free conditions. Notably, the nucleophilic character of phosphite-ligated boryl radicals enab...

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (51), p.9452-9457
Main Authors: Choi, Wonjun, Kim, Minseok, Lee, Kangjae, Park, Seongjin, Hong, Sungwoo
Format: Article
Language:English
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Summary:The photoinduced C4-selective C–H borylation of pyridines was achieved using electron donor–acceptor complexes derived from a Lewis base and N-amidopyridinium salts under external oxidant- and photocatalyst-free conditions. Notably, the nucleophilic character of phosphite-ligated boryl radicals enables addition of a radical to position C4 of pyridinium salts to afford C4-borylated heteroarenes that are otherwise difficult to obtain. This approach provides a versatile platform for the installation of both phosphite- and amine-coordinated boron groups on a series of pyridines under mild conditions, demonstrating excellent C4-positional selectivity for the pyridine scaffolds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03882