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铜催化实现烯烃的发散性C-H氧化自由基官能团化以引入叔烷基结构单元

Divergent C-H Oxidative Radical Functionalization of Olefins to Install Tertiary Alkyl Motifs Enabled by Copper Catalysis.

作者信息

Tian Ming-Qing, Wang Cong, Hu Xu-Hong, Loh Teck-Peng

机构信息

Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials , Nanjing Tech University , Nanjing 211816 , China.

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences , Nanyang Technological University , Singapore 637371 , Singapore.

出版信息

Org Lett. 2019 Mar 15;21(6):1607-1611. doi: 10.1021/acs.orglett.9b00142. Epub 2019 Feb 22.

DOI:10.1021/acs.orglett.9b00142
PMID:30793908
Abstract

An efficient tertiary alkylation reaction of olefins with 1,3-dicarbonyl compounds was developed by virtue of copper catalyst without the use of expensive ligands or additives. In contrast to alkyl Heck-type reaction, alkyl halide is not required. Notably, by varying the nitrogen and air atmosphere, the reaction selectively produces alkylation and alkylation-oxygenation products, respectively. Initial investigations revealed that an α-carbonyl alkyl radical species might be involved in the process.

摘要

借助铜催化剂,开发了一种烯烃与1,3 - 二羰基化合物的高效叔烷基化反应,无需使用昂贵的配体或添加剂。与烷基Heck型反应不同,不需要卤代烃。值得注意的是,通过改变氮气和空气气氛,该反应分别选择性地生成烷基化产物和烷基化 - 氧化产物。初步研究表明,该过程可能涉及α - 羰基烷基自由基物种。

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