Pyridine N-oxides as HAT reagents for photochemical C-H functionalization of electron-deficient heteroarenes

13 June 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Pyridine N-oxides only recenly marked their presence in the photocatalysis outbreak, mainly serving as oxypyridinium salt precursors. Herein, their unique reactivity as a hydrogen atom transfer reagent in photochemical, Minisci-type alkylation of electron-deficient heteroarenes is unveiled. The formation of an EDA complex between a heterocyclic substrate and N-oxide precludes the need for a photocatalyst. The developed method allows for a broad range of radical precursors to be used, namely alkanes, alkenes, amides, and ethers, for efficient alkylation of azines.


pyridine N-oxides


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