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Palladium-Catalyzed Regioselective C–H Alkenylation of Arylacetamides via Distal Weakly Coordinating Primary Amides as Directing Groups
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-01-11 00:00:00 , DOI: 10.1021/acs.joc.7b02618
Yogesh Jaiswal 1 , Yogesh Kumar 1 , Amit Kumar 1
Affiliation  

Herein we disclose the efficient Pd(II)-catalyzed and regioselective ortho C–H alkenylation of arylacetamide derivatives, viz. weakly coordinating aliphatic primary amides. This protocol utilizes ubiquitous free primary amides as the directing group and circumvents two troublesome steps of installation and removal of an external auxiliary. This strategy directly enables the incorporation of a synthetically versatile olefin in the products in moderate to good yields with regio- and distereoselectivity. The alkenylated acetamides can be easily manipulated and further transformed into a variety of useful derivatives.

中文翻译:

钯通过弱弱配位伯酰胺作为指导基团催化芳基乙酰胺的区域选择性C–H烯基化

在这里,我们公开了芳基乙酰胺衍生物的有效Pd(II)催化和区域选择性邻位C-H烯基化反应,即。弱配位的脂肪族伯酰胺。该方案利用无处不在的游离伯酰胺作为指导基团,规避了安装和拆卸外部助剂的两个麻烦步骤。该策略直接使得能够以中等至良好的产率将合成通用的烯烃掺入产物中,并具有区域选择性和立体选择性。烯基化乙酰胺可以容易地操作,并进一步转化为多种有用的衍生物。
更新日期:2018-01-11
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