Synergistic Br?nsted Base/Photoredox-Catalyzed Three-Component Coupling with Malonates to Synthesizeδ-Hydroxy Esters and δ-Keto Esters

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外文摘要：Multicomponent alkene 1,2-dicarbofunctionalizations(DCFs)have emerged as a powerful strategy to rapidly incorporate both two carbon subunits across one C—C double bond in one step for enhancing molecular complexity and diversity.To the best of our knowledge,there is only one report on photoredox-catalyzed three-component DCFs with malonates through the radical-radical cross-coupling,while photoredox-catalyzed radical-polar crossover(RPC)-type DCFs with malonates were still rare.Herein,we describe a redox-neutral RPC-type 1,2-dialkylation of styrenes with malonates and aldehydes through the synergistic Brønsted base/photore-dox catalysis system.This transition-metal-free strategy provides an efficient and clean approach to a broad variety of 6-hydroxy esters and also features exceptionally mild conditions,wide compatibility of substrate scope and functional groups,and high atomic econo-my.Moreover,three-component 1,2-alkylacylation from the same starting materials was achieved in one-pot manner through such RPC-type coupling and subsequent two-electron oxidation process,providing a set of δ-keto esters of interest in pharmaceutical re-search.

外文关键词：

Alkene difunctionalizationPhotoredox catalysisMalonatesRadical reactionsC—C couplingSynthetic methodsAldehydesAlkylationMulticomponent reactions

作者：

Ting Li、Wei Wang、Ming Dong、Zhijie Zhang、Sha Yu、Zhengchu Chen、Siping Wei、Dong Yi

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作者单位：

Green Pharmaceutical Technology Key Laboratory of Luzhou City,Central Nervous System Drug Key Laboratory of Sichuan Province,School of Pharmacy,Southwest Medical University,Luzhou,Sichuan 646000,China

Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province,Luzhou,Sichuan 646000,China

基金：

National Natural Science Foundation of ChinaNational Natural Science Foundation of ChinaScience and Technology Program of Sichuan ProvinceScience and Technology Program of Luzhou CityScience and Technology Program of Luzhou CityOpen Project Program of Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province

项目编号：

22101237221712332022NSFSC12192021-SYF-342023LZXNYDJ019HYX21003

出版年：

2024

DOI：

10.1002/cjoc.202300683

中国化学(英文版)

中国化学会上海有机化学研究所

中国化学(英文版)

CSTPCD

影响因子：0.848

ISSN：1001-604X

年,卷(期)：2024.42(9)