Indium-promoted butenolide synthesis through consecutive C-C and C-O bond formations in aqueous tetrahydrofuran enabled by radicals
Indium-promoted butenolide synthesis through consecutive C-C and C-O bond formations in aqueous tetrahydrofuran enabled by radicals
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DOI：
10.1039/d3qo00133d
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发表时间：
2023-02-27
影响因子：
5.4
通讯作者：
Almendros，Pedro
中科院分区：
文献类型：
--
作者：
Yanai，Hikaru;Marquez，M. Rosa;Almendros，Pedro
完成了铟促进的(吲哚-3-基)-2-氧基乙醛的内酯化反应，该反应允许在水环境中合成取代的γ-亚甲基丁烯内酯。这一过程与公认的金属介导的不饱和有机卤化物和羰基的反应性形成了鲜明的对比。水介质的使用和简易的纯化轮廓使我们的协议成为一种方便和可持续的合成策略。通过密度泛函理论计算，提出了一个合理的反应途径。
An indium-promoted lactonization of (indol-3-yl)-2-oxoacetaldehydes, which allows the synthesis of substituted γ-methylenebutenolides in an aqueous environment, has been accomplished. This process is in clear contrast with the established metal-mediated reactivity of unsaturated organic halides and carbonyls. The use of an aqueous medium and the facile purification profile make our protocol a convenient and sustainable synthetic strategy. A plausible reaction pathway has been proposed with the help of density functional theory calculations.