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镍催化的α-氨基酸硫代酯选择性脱羰基反应:巯基的氨甲基化。

Nickel-Catalyzed Selective Decarbonylation of α-Amino Acid Thioester: Aminomethylation of Mercaptans.

机构信息

College of Pharmaceutical Sciences, Soochow University, Suzhou 215123, China.

出版信息

J Org Chem. 2021 Sep 3;86(17):12148-12157. doi: 10.1021/acs.joc.1c01480. Epub 2021 Aug 16.

Abstract

The nickel-catalyzed aminomethylation of mercaptans has been disclosed that offers efficient and expedient access to synthesize α-aminosulfides. The intramolecular fragment coupling shows excellent chemoselectivity. This transformation shows good functional-group compatibility, tolerates a wide range of electron-withdrawing, electron-neutral, and electron-donating substituents in this process, and can serve as a powerful synthetic tool for the synthesis of α-aminosulfides at a gram scale. Thus, the newly developed methodology enables a facile route for C-S bond formation in a straightforward fashion.

摘要

镍催化的硫醇的氨甲基化反应已经被揭示,它为合成α-氨基硫化物提供了高效、便捷的途径。分子内片段偶联显示出优异的化学选择性。这种转化对功能基团具有很好的兼容性,在这个过程中可以容忍广泛的吸电子、电子中性和供电子取代基,并且可以作为在克级规模上合成α-氨基硫化物的有力合成工具。因此,新开发的方法为 C-S 键的形成提供了一种直接的简便途径。

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