Nickel-catalyzed amination of aryl halides: An exogenous ligand-free approach to primary arylamines using TMSN3

IF 6.5 1区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Catalysis Pub Date : 2025-06-19 DOI:10.1016/j.jcat.2025.116284

Jiawei Huang, Xiaoman Li, Zhigang Lei, Liang Xu, Shuai Liu

引用次数: 0

Abstract

Efficiently synthesizing primary amines continues to pose a significant challenge in the field of synthetic chemistry. This study reports a highly effective nickel-catalyzed amination of aryl halides using trimethylsilyl azide (TMSN₃) as the nitrogen source, facilitated by methoxytrimethylsilane (MeO₃SiH) under thermal conditions. Notably, this reaction proceeds without the need for an exogenous ligand and under mild conditions. Mechanistic investigations reveal that (MeO)₃SiH promotes the formation of Ni(I) species, which cycle through Ni(I)/Ni(III) intermediates, driving the amination process efficiently.

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镍催化芳基卤化物胺化：利用TMSN3制备伯芳胺的外源无配体方法

高效合成伯胺一直是合成化学领域的一大挑战。本研究报道了以三甲基硅酰叠氮化物（TMSN3）为氮源，甲氧基三甲基硅烷（MeO3SiH）在热条件下催化芳基卤化物的高效胺化反应。值得注意的是，该反应不需要外源配体，并且在温和的条件下进行。机理研究表明，（MeO）3SiH促进了Ni(I)的形成，Ni(I)/Ni（III）中间体循环，有效地驱动了胺化过程。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Catalysis 工程技术-工程：化工

CiteScore

12.30

自引率

5.50%

发文量

447

审稿时长

31 days

期刊介绍： The Journal of Catalysis publishes scholarly articles on both heterogeneous and homogeneous catalysis, covering a wide range of chemical transformations. These include various types of catalysis, such as those mediated by photons, plasmons, and electrons. The focus of the studies is to understand the relationship between catalytic function and the underlying chemical properties of surfaces and metal complexes. The articles in the journal offer innovative concepts and explore the synthesis and kinetics of inorganic solids and homogeneous complexes. Furthermore, they discuss spectroscopic techniques for characterizing catalysts, investigate the interaction of probes and reacting species with catalysts, and employ theoretical methods. The research presented in the journal should have direct relevance to the field of catalytic processes, addressing either fundamental aspects or applications of catalysis.