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铁催化的 C-O 硅烷化反应:构建 Csp-Si 键的通用方法。

C-O Bond Silylation Catalyzed by Iron: A General Method for the Construction of Csp-Si Bonds.

机构信息

Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.

Sichuan Key Laboratory of Medical Imaging & Department of Chemistry, School of Preclinical Medicine, North Sichuan Medical College, Nanchong, Sichuan 637000, China.

出版信息

Org Lett. 2020 Apr 3;22(7):2669-2674. doi: 10.1021/acs.orglett.0c00633. Epub 2020 Mar 13.

Abstract

The iron-catalyzed construction of Csp-Si bonds via unreactive C-O bonds possesses a challenging topic in organic chemistry. Herein we report an iron-catalyzed silylation of aryl and alkenyl carbamates via C-O bond activation. This protocol features high efficiency and a broad substrate scope, enabling the late-stage silylation of biorelevant compounds and thus providing a good method to access valuable motifs in medicinal chemistry. Moreover, this protocol enables orthogonal transformations of phenol derivatives and also allows for the synthesis of multisubstituted arenes through the carbamate group as the directing group.

摘要

通过惰性 C-O 键构建 Csp-Si 键在有机化学中是一个具有挑战性的课题。在此,我们报告了通过 C-O 键活化实现芳基和烯基氨基甲酸酯的铁催化硅烷化反应。该方法具有高效性和广泛的底物范围,能够对生物相关化合物进行晚期硅烷化,从而为药物化学中提供有价值的基序提供了一种很好的方法。此外,该方法还可以实现酚衍生物的正交转化,并且可以通过氨基甲酸酯作为导向基团合成多取代芳烃。

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