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通过光氧化还原/镍协同催化实现烯烃的三组分区域选择性芳基和烯基氨基烷基化反应

Three-Component Regioselective Aryl- and Alkenyl-Aminoalkylation of Alkenes via Cooperative Photoredox/Nickel Catalysis.

作者信息

Ye Fu, Yuan Weiming

机构信息

Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), 1037 Luoyu Road, Wuhan 430074, P. R. China.

出版信息

J Org Chem. 2024 Dec 6;89(23):17708-17719. doi: 10.1021/acs.joc.4c02482. Epub 2024 Nov 25.

Abstract

Recently, metallaphotoredox-catalyzed alkene dicarbofunctionalization reactions have been extensively investigated. Most cases are related to alkyl-arylation processes by conjugate coupling of alkyl radical precursors and aryl electrophiles across alkenes. By contrast, reported examples of alkylvinylation by coupling of vinyl electrophiles are largely limited. Herein, we represent a three-component aminoalkyl-vinylation of alkenes enabled by photoredox/nickel catalysis. This redox-neutral protocol exhibits broad substrate scope and good chemo-, regio- and /-stereoselectivity. A series of valuable α-vinyl γ-amino acid derivatives are conveniently synthesized by the assembly of readily available starting materials.

摘要

最近,金属光氧化还原催化的烯烃双碳官能化反应受到了广泛研究。大多数情况涉及通过烷基自由基前体与芳基亲电试剂在烯烃上的共轭偶联进行烷基芳基化过程。相比之下,通过乙烯基亲电试剂偶联进行烷基乙烯基化的报道实例非常有限。在此,我们展示了一种通过光氧化还原/镍催化实现的烯烃三组分氨基烷基乙烯基化反应。这种氧化还原中性的方法具有广泛的底物范围以及良好的化学、区域和对映立体选择性。通过组装易得的起始原料,可以方便地合成一系列有价值的α-乙烯基γ-氨基酸衍生物。

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