Photoredox phosphonomethylation/cyclization of alkenes enabled by an EDA complex

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2026-07-01 Epub Date: 2026-05-09 DOI:10.1039/d6qo00468g

Yang Zheng, Jiayao Zheng, Wenxue Zhao, Kai Yang, Qingqing Chen, Xiaohui Wang, Jiahui Jia, Cong Du, Chenxu Wei, Fei Chen, Xiaobo Pan

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Abstract

The phosphonomethyl unit is an important functional group in medicinal chemistry. ICH₂PO(R¹R²) is a commercially available phosphonomethylation reagent. However, the synthesis of phosphonomethyl-substituted cyclic molecules by using ICH₂PO(R¹R²) mainly relies on noble metal-catalyzed methods. Herein, the photoredox phosphonomethylation/cyclization of alkenes has been developed. Mechanistically, the electron donor–acceptor (EDA) complex formed in situ between ICH₂PO(R¹R²) and 1,4-diazabicyclo[2.2.2]octane (DABCO) is key to this reaction. This method does not require photocatalysts, oxidants, or reducing agents and operates under mild conditions, making it suitable for the late-stage modification of drug molecules.

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EDA配合物使烯烃的光氧化还原磷甲基化/环化

磷甲乙基是药物化学中一种重要的官能团。ICH2PO（R1R2）是一种市售的磷酸化甲基化试剂。然而，利用ICH2PO（R1R2）合成磷代甲基环分子主要依靠贵金属催化的方法。本文研究了烯烃的光氧化还原膦甲基化/环化反应。从机理上说，在ICH2PO（R1R2）和1,4-重氮杂环[2.2.2]辛烷（DABCO）之间原位形成的电子供体-受体（EDA）复合物是该反应的关键。该方法不需要光催化剂、氧化剂或还原剂，并且在温和的条件下操作，使其适合于药物分子的后期修饰。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic chemistry frontiers : an international journal of organic chemistry

CiteScore

7.80

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0.00%

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