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钯催化的烯烃连接芳基卤化物的二硅基化和二锗基化反应:直接合成多功能硅基化和锗基化杂环化合物

Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles.

作者信息

Wollenburg Marco, Bajohr Jonathan, Marchese Austin D, Whyte Andrew, Glorius Frank, Lautens Mark

机构信息

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.

Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.

出版信息

Org Lett. 2020 May 1;22(9):3679-3683. doi: 10.1021/acs.orglett.0c01169. Epub 2020 Apr 20.

Abstract

A method for the palladium-catalyzed disilylation and digermanylation of aryl halides bearing a tethered alkene has been developed. The mechanism is thought to proceed Heck-type cyclization, followed by C-H activation, resulting in a reactive fused-palladacycle. A wide variety of disilylated and digermanylated heterocycles are obtained from readily available aryl halides in high yields with various functional groups. Moreover, the developed protocol proved to be highly diastereoselective.

摘要

已开发出一种用于钯催化带有连接烯烃的芳基卤化物的二硅基化和二锗基化的方法。据认为,该机理是通过Heck型环化,然后进行C-H活化,从而生成一种活性稠合钯环。从易于获得的芳基卤化物出发,能以高产率得到带有各种官能团的多种二硅基化和二锗基化杂环化合物。此外,所开发的方案被证明具有高度的非对映选择性。

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