Oxydiazomethylation of Alkenes <i>via</i> Photoredox Catalysis
Ying Zeng, Xiaochan Zheng, Lixing Shen, Yaru Jing, Shaoyong Chen, Zhongfeng Luo, Zhuofeng Ke, Haisheng Xie, Jun-Shan Liu, Huanfeng Jiang, Wei Zeng
Abstract
Abstract 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‐oxydiazomethylation of alkenes through visible‐light photoredox catalysis. This process exploits photocatalyzed strategy to convert alkenes to γ‐formyloxyl‐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 DMF and H 2 O to allow for this transformation.