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镍催化芳基碘化物与杂芳族硫醚通过C-S键裂解的脱硫交叉偶联反应。

Nickel-Catalyzed Desulfurative Cross-Coupling of Aryl Iodides with Heteroaromatic Thioethers via C-S Bond Cleavage.

作者信息

Zhu Pingliang, Zhao Yu, Ling Shaowen, Xu Baolong, Liu Hui, Li Xinjin, Sun Feng-Gang

机构信息

School of Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. China.

出版信息

J Org Chem. 2024 Sep 6;89(17):12001-12009. doi: 10.1021/acs.joc.4c00678. Epub 2024 Aug 15.

Abstract

Herein, we present a Ni-catalyzed direct cross-coupling of heteroaromatic thioethers with aryl iodides via selective C(sp)-S bond cleavage under reductive conditions, thereby providing various biaryl frameworks with high efficiency. Mechanistic studies suggested Mo(CO) played a crucial role in facilitating the activation of the C(sp)-S bond. This protocol demonstrated a wide substrate scope, operational simplicity, and good functional group compatibility. Furthermore, the utility of this reaction was highlighted by facile scale-up and sequential modification of heteroaryl frameworks.

摘要

在此,我们展示了一种镍催化的杂芳基硫醚与芳基碘化物在还原条件下通过选择性C(sp)-S键裂解进行的直接交叉偶联反应,从而高效地提供了各种联芳基骨架。机理研究表明,Mo(CO)在促进C(sp)-S键的活化中起关键作用。该方法具有广泛的底物范围、操作简便以及良好的官能团兼容性。此外,该反应的实用性通过易于放大和杂芳基骨架的连续修饰得以凸显。

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