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通过氧化钯(II)催化的Heck型偶联从炔烃快速构建烯炔

Expeditious Enyne Construction from Alkynes via Oxidative Pd(II) Catalyzed Heck-Type Coupling.

作者信息

Hadi Victor, Yoo Kyung Soo, Jeong Min, Jung Kyung Woon

机构信息

Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661.

出版信息

Tetrahedron Lett. 2009 May 20;50(20):2370-2373. doi: 10.1016/j.tetlet.2009.02.217.

DOI:10.1016/j.tetlet.2009.02.217
PMID:20161498
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2796801/
Abstract

The enyne, ubiquitous in natural products, can be a challenge to generate since these moieties require many synthetic transformations to assemble them. We developed a simpler protocol to construct enynes while we found that this oxidative reaction was tolerant in substrate scope. In addition, the utility of this reaction was demonstrated through the attempt in synthesizing antifungal agent Lamisi.

摘要

烯炔结构在天然产物中普遍存在,但由于这些部分需要许多合成转化来组装,因此生成它们可能具有挑战性。我们开发了一种更简单的方案来构建烯炔,同时我们发现这种氧化反应在底物范围上具有耐受性。此外,通过尝试合成抗真菌剂拉米西,证明了该反应的实用性。

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本文引用的文献

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Nickel-catalyzed Mizoroki-Heck- versus Michael-type addition of organoboronic acids to alpha,beta-unsaturated alkenes through fine-tuning of ligands.通过配体的微调实现镍催化有机硼酸对α,β-不饱和烯烃的 Mizoroki-Heck 反应与迈克尔型加成反应
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Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.氧化钯(II)催化:一种在无碱和含氮配体条件下用于碳-碳键形成的高效且化学选择性交叉偶联方法。
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Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: key involvement of a palladium peroxo complex.钯催化芳基硼酸均偶联反应的机理:钯过氧配合物的关键作用
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Novel 3-oxa lipoxin A4 analogues with enhanced chemical and metabolic stability have anti-inflammatory activity in vivo.具有增强的化学和代谢稳定性的新型3-氧杂脂oxin A4类似物在体内具有抗炎活性。
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Synthesis of methyl (5S,6R,7E,9E,11Z,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-7,9,11,13-hexadecatetraenoate, an analogue of 15R-lipoxin A4.(5S,6R,7E,9E,11Z,13E,15S)-16-(4-氟苯氧基)-5,6,15-三羟基-7,9,11,13-十六碳四烯酸甲酯的合成,15R-脂氧素A4的类似物
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