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微波辐射下过渡金属催化的芳基炔酰胺与甲基芳烃的氧化螺环化反应

Transition-metal catalyzed oxidative spirocyclization of -aryl alkynamides with methylarenes under microwave irradiation.

作者信息

Yuan Jin-Wei, Mou Chen-Xu, Zhang Yang, Hu Wen-Yu, Yang Liang-Ru, Xiao Yong-Mei, Mao Pu, Zhang Shou-Ren, Qu Ling-Bo

机构信息

School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001, P. R. China.

Henan Key Laboratory of Nanocomposites and Applications, Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006, P. R. China.

出版信息

Org Biomol Chem. 2021 Dec 8;19(47):10348-10358. doi: 10.1039/d1ob01970h.

Abstract

A practical synthetic route to construct a variety of 3-benzyl spiro[4,5]trienones was developed transition-metal Cu/Ag-catalyzed oxidative -annulation of activated alkynes with unactivated toluenes using TBPB as an oxidant under microwave irradiation. This method allows the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, -carbocyclization and dearomatization. The advantages of this protocol are its operational simplicity and broad substrate scope, and the ability to afford the desired products in moderate to good yields.

摘要

开发了一种实用的合成路线,用于构建多种3-苄基螺[4,5]三烯酮,该路线是在微波辐射下,以TBPB为氧化剂,通过过渡金属铜/银催化未活化的甲苯与活化炔烃进行氧化环化反应。该方法能够通过C-H氧化偶联、碳环化和脱芳构化序列,在单一反应中形成两个碳-碳键和一个碳-氧键。该方案的优点是操作简单、底物范围广,并且能够以中等至良好的产率得到所需产物。

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