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通过α-氧代羧酸的脱羧加成实现烯烃的光介导氢(氘)酰化反应

Photomediated Hydro(deutero)acylation of Olefins by Decarboxylative Addition of α-Oxocarboxylic Acids.

作者信息

Gao Fan, Liao Zhi-Yu, Ye Yu-Hang, Yu Qian-Hui, Yang Cui, Luo Qing-Yu, Du Fei, Pan Bin, Zhong Wen-Wu, Liang Wu

机构信息

College of Pharmacy, Chongqing Medical University, Chongqing 400016, China.

College of Pharmacy, Third Military Medical University, Shapingba, Chongqing 400038, China.

出版信息

J Org Chem. 2024 Feb 16;89(4):2741-2747. doi: 10.1021/acs.joc.3c02838. Epub 2024 Feb 1.

Abstract

Acyl radicals have been generated from the decarboxylation of α-oxocarboxylic acids by using a readily accessible organic pyrimidopteridine photoredox catalyst under ultraviolet-A (UV-A) light irradiation. These reactive acyl radicals were smoothly added to olefins such as styrenes and diverse Michael acceptors, with the assistance of HO/DO as hydrogen donors, enabling easy access to a diverse range of ketones/β-deuterio ketones. A wide range of α-oxocarboxylic acids are compatible with this reaction, which shows a reliable, atom-economical, and eco-friendly protocol. Furthermore, postsynthetic diversifications and applications are presented.

摘要

通过在紫外-A(UV-A)光照射下使用易于获得的有机嘧啶并蝶啶光氧化还原催化剂,从α-氧代羧酸的脱羧反应中产生了酰基自由基。在HO/DO作为氢供体的辅助下,这些活性酰基自由基能顺利地加成到烯烃(如苯乙烯)和各种迈克尔受体上,从而能够轻松获得各种酮类/β-氘代酮类。多种α-氧代羧酸与该反应兼容,该反应展示了一种可靠、原子经济且环保的方案。此外,还介绍了合成后的多样化反应及应用。

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