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双功能 Pd 催化的多组分反应:通过亲电试剂中氧原子的反转化学。

Dual Functional Pd-Catalyzed Multicomponent Reaction by Umpolung Chemistry of the Oxygen Atom in Electrophiles.

机构信息

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, China 200062.

出版信息

J Org Chem. 2021 May 7;86(9):6847-6854. doi: 10.1021/acs.joc.0c02413. Epub 2021 Apr 12.

DOI:10.1021/acs.joc.0c02413
PMID:33844915
Abstract

A Pd-catalyzed multicomponent reaction was developed by trapping oxomium ylide with nitrosobenzene via Pd-promoted umpolung chemistry. The Pd catalyst plays two important roles: diazo compound decomposed catalyst and Lewis acid for the activation of nitrosobenzene. This strategy provides some insight into a new way for discovery of multicomponent methodology to construct complex molecules. The developed method also provides rapid access to a series of -(2-oxy) hydroxylamine derivatives, which exhibit good anticancer activity in osteosarcoma cells.

摘要

Pd 催化的多组分反应通过 Pd 促进的反转化学作用将氧化锇叶立德与亚硝基苯捕获,从而得以开发。Pd 催化剂发挥了两个重要作用:重氮化合物分解催化剂和路易斯酸,用于激活亚硝基苯。该策略为发现多组分方法构建复杂分子提供了新的思路。所开发的方法还可以快速获得一系列-(2-氧基)羟胺衍生物,它们在骨肉瘤细胞中表现出良好的抗癌活性。

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