Hydroxyl-Diazomethylation of Alkenes via Photoredox Catalysis

27 December 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


α-Diazoesters belong to significantly important carbenoid precursors in synthetic chemistry, diazomethylation-based difunctionalization of alkenes is highly valuable but remain nontrivial. Herein, we reported a general and modular approach for the direct 1,2-hydroxyl-diazomethylation of alkenes through visible-light photoredox catalysis. This process exploits photocatalyzed strategy to convert alkenes to γ-hydroxyl-α-diazoesters using α-diazo iodonium salts as carbyne precursors, featuring wide substrate tolerance and broad late-stage diversifications. Mechanistic studies suggest that the formation of γ-carbocation-tethered α-diazoesters plays a crucial role in trapping H2O to allow for this transformation.


Photoredox Catalysis
Low-valent carbon species


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