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学科主题: 金属有机化学
题名: Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: A simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization
其他题名: 钯催化的炔-丙炔醇碳酸酯与硼酸的串联反应: 通过联烯促进的电环化反应合成芳香并环化合物的方法
作者: Wang F(王峰) ; Tong XF(童晓峰) ; Cheng J(成奖) ; Zhang ZG(张兆国)
通讯作者: 张兆国
刊名: Chem.-Eur. J.
发表日期: 2004
卷: 10, 期:21, 页:5338-5344
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所金属有机化学实验室
英文摘要: The palladium-catalyzed tandem reactions of yne-propargylic carbonates with aryl boronic acids, 2-furyl boronic acid, and 2-thiopheneboronic acid, followed by 6pi-electrocyclization to give fused ring aromatic products such as naphthalene, benzofuran, and benzothiophene derivatives are realized. Screening of the reaction conditions revealed that the combination of [Pd(PPh3)(4)] in THF gave the best results in terms of reactivity and product yields in the reaction of yne-propargylic carbonates with phenylboronic acid. The reaction is sensitive toward steric hindrance when substituted phenylboronic acids are emplyed. However, when we take 2-furyl boronic acid as the organometallic reagent, most substrates perform very well to give benzofuran derivatives. In addition, 2-thiopheneboronic acid is also a very effective coupling reagent to give bezothiophenes in high yields. A mechanism is proposed that involves the formation of an allenylpalladium complex from Pd-0 and propargylic carbonate, followed by insertion of an intramolecular triple bond and the Suzuki coupling reaction, and then electrocyclization.
语种: 英语
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WOS记录号: WOS:000224783800008
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/27609
Appears in Collections:上海有机化学研究所_期刊论文

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Recommended Citation:
Wang F,Tong XF,Cheng J,et al. Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: A simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization[J]. Chem.-Eur. J.,2004,10(21):5338-5344.
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