Copper-Catalyzed Ring-Opening Silylation of Benzofurans with Disilane

被引：22

作者：

Saito, Hayate ^{[1
]}

Nogi, Keisuke ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 34期

关键词：

benzofurans; copper catalysts; DFT calculations; nucleophilic addition; silylation; BOND ACTIVATION; ORGANOSILICON COMPOUNDS; AROMATIC METAMORPHOSIS; DENSITY FUNCTIONALS; GRIGNARD-REAGENTS; COUPLING REACTION; BIS-SILYLATION; ENOL ETHERS; SI BOND; CHEMISTRY;

D O I：

10.1002/anie.201806237

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic ring-opening silylation of benzofurans has been achieved by employing a copper catalyst and 1,2-di-tert-butoxy-1,1,2,2-tetramethyldisilane, which could be easily prepared and handled without special care. The reaction afforded (E)-o-(beta-silylvinyl)phenols with complete stereoselectivity. The scope of benzofurans was well explored, and functional groups such as chloro, fluoro, and acetal were compatible with the reaction conditions. DFT calculations were used to determine the energy profile of the silylation and the origin of the stereoselectivity. The silylated product was proven to be useful as a synthetic intermediate and subsequently underwent transformations such as Pd-catalyzed cross-coupling with iodoarenes.

引用

页码：11030 / 11034

页数：5

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