Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ-Lactones Mediated by Molecular Iodine under Visible Light Irradiation,Advanced Synthesis & Catalysis

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Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ-Lactones Mediated by Molecular Iodine under Visible Light Irradiation
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-09-11 10:43:20 , DOI: 10.1002/adsc.201700809
Saki Maejima ₁ , Eiji Yamaguchi ₁ , Akichika Itoh ₁

Affiliation

The iodine-mediated intermolecular C−C bond-forming/esterification reaction of various alkenes including α-olefins with malonates under irradiation using a compact fluorescent lamp has been developed to synthesize γ-lactones in moderate to excellent yields. The method developed in this research shows broad substrate scope and moderate diastereoselectivity and constructs valuable polyfunctionalized γ-lactones. Furthermore, the developed methodology was comprehensively studied by performing several control experiments, radical trapping, and radical clock experiments. These experiments showed that sequential iodination by an iodine radical is triggered for the following C−C bond-forming reaction.γ

中文翻译：

可见光照射下烯烃与丙二酸酯的分子间串联加成/酯化反应导致分子碘介导的γ-内酯

已经开发出在紧凑型荧光灯的照射下，碘介导的各种烯烃（包括α-烯烃）与丙二酸酯的分子间C-C键形成/酯化反应，能够以中等至极好的收率合成γ-内酯。本研究开发的方法显示出较宽的底物范围和适度的非对映选择性，并构建了有价值的多官能化γ-内酯。此外，通过执行几个控制实验，自由基捕获和自由基时钟实验，对所开发的方法进行了全面研究。这些实验表明，随后的C-C键形成反应触发了由碘自由基进行的顺序碘化反应。

更新日期：2017-09-11

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