Oxydiazomethylation of Alkenes via Photoredox Catalysis

被引：1

作者：

Zeng, Ying ^{[1
]}

Zheng, Xiaochan ^{[2
]}

Shen, Lixing ^{[1
]}

Jing, Yaru ^{[3
]}

Chen, Shaoyong ^{[1
]}

Luo, Zhongfeng ^{[1
]}

Ke, Zhuofeng ^{[3
]}

Xie, Haisheng ^{[1
]}

Liu, Junshan ^{[2
]}

Jiang, Huanfeng ^{[1
]}

Zeng, Wei ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, 381 Wushan Rd, Guangzhou 510641, Peoples R China

[2] Southern Med Univ, Sch Tradit Chinese Med, Guangdong Prov Key Lab Chinese Med Pharmaceut, 1023 South Shatai Rd, Guangzhou 510515, Peoples R China

[3] Sun Yat Sen Univ, Sch Mat Sci & Engn, PFCM Lab, 132 Waihuan East Rd, Guangzhou 510006, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2025年 / 31卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Alkenes; alpha-diazo onium salts; Oxydiazomethylation; gamma-formyloxyl-alpha-diazoesters; Photocatalysis; C-H BONDS; REARRANGEMENT; INSERTION;

D O I：

10.1002/chem.202403509

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-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 gamma-formyloxyl-alpha-diazoesters using alpha-diazo iodonium salts as carbyne precursors, featuring wide substrate tolerance and broad late-stage diversifications. Mechanistic studies suggest that the formation of gamma-carbocation-tethered alpha-diazoesters plays a crucial role in trapping DMF and H2O to allow for this transformation.

引用

页数：8

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