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Ferric chloride–catalyzed deoxygenative chlorination of carbonyl compounds: A comparison of chlorodimethylsilane and dichloromethylsilane system
Journal of Chemical Research ( IF 1.4 ) Pub Date : 2020-05-14 , DOI: 10.1177/1747519820910959
Bing-Han Xing 1 , Xuan-Xuan Zhao 1 , Yu-Jun Qin 1 , Pu Zhang 1 , Zhi-Xin Guo 1
Affiliation  

Deoxygenative chlorination of carbonyl compounds using the HMe2SiCl/FeCl3/EtOAc and HMeSiCl2/FeCl3/EtOAc systems has been systemically investigated. The HMe2SiCl-FeCl3 system showed the advantages of good substrate applicability, mild reaction conditions, simple operation, low cost, and easy availability of raw materials. Also, it provided a simple and efficient synthesis route for carbonyl deoxychlorination via a one-pot method. Using the HMeSiCl2/FeCl3/EtOAc system, the β-methylchalcone derivative could be obtained in good yields in addition to obtaining the chlorinated compound. Finally, two plausible reaction routes were proposed to describe the formation of the chlorinated compound and the β-methylchalcone derivative.

中文翻译:

三氯化铁催化羰基化合物的脱氧氯化:氯二甲基硅烷和二氯甲基硅烷体系的比较

已经系统地研究了使用 HMe2SiCl/FeCl3/EtOAc 和 HMeSiCl2/FeCl3/EtOAc 系统对羰基化合物进行脱氧氯化。HMe2SiCl-FeCl3体系具有底物适用性好、反应条件温和、操作简单、成本低、原料易得等优点。为羰基脱氧氯化的一锅法提供了一条简单有效的合成路线。使用HMeSiCl2/FeCl3/EtOAc体系,除了获得氯化化合物外,还可以以良好的收率获得β-甲基查尔酮衍生物。最后,提出了两种可能的反应路线来描述氯化化合物和 β-甲基查尔酮衍生物的形成。
更新日期:2020-05-14
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