The selective N-alkylation of amines with alcohols via the borrowing hydrogen strategy represents a prominent sustainable catalytic method, which produces water as the only by-product and is ideally suited for the catalytic transformation of widely available alcohol reaction partners that can be derived from renewable resources. Intensive research has been devoted to the development of novel catalysts that are mainly based on expensive noble metals. However, the availability of homogeneous or heterogeneous non-precious metal catalysts for this transformation is very limited. Herein we present a highly active and remarkably easy-to-prepare Ni based catalyst system for the selective N-alkylation of amines with alcohols, that is in situ generated from Ni(COD)₂ and KOH under ligand-free conditions. This novel method is very efficient for the functionalization of aniline and derivatives with a wide range of aromatic and aliphatic alcohols as well as diols and exhibits excellent functional group tolerance including halides, benzodioxane and heteroaromatic groups. Several TEM measurements combined with elemental analysis were conducted in order to gain insight into the nature of the active catalyst and factors influencing reactivity.

中文翻译：

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醇与 镍的高效镍催化N-烷基化†

通过借用氢策略使胺与醇选择性地进行N烷基化反应是一种突出的可持续催化方法，该方法产生水作为唯一的副产物，非常适合可广泛衍生自可再生能源的醇反应伙伴的催化转化资源。集中研究致力于开发主要基于昂贵的贵金属的新型催化剂。但是，用于这种转化的均相或非均相非贵金属催化剂的可用性非常有限。本文中，我们提出了一种高活性且非常易于制备的镍基催化剂体系，用于将胺与醇选择性地进行N-烷基化，该反应是就地进行的。在无配体条件下由Ni（COD）₂和KOH生成。这种新方法对于苯胺及其衍生物与各种芳香族和脂肪族醇以及二醇的官能化非常有效，并且具有出色的官能团耐受性，包括卤化物，苯并二恶烷和杂芳族基团。为了结合活性催化剂的性质和影响反应活性的因素，进行了几种TEM测量和元素分析的结合。