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Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen.
Chemical Reviews ( IF 51.4 ) Pub Date : 2020-08-19 , DOI: 10.1021/acs.chemrev.0c00248 Torsten Irrgang 1 , Rhett Kempe 1
Chemical Reviews ( IF 51.4 ) Pub Date : 2020-08-19 , DOI: 10.1021/acs.chemrev.0c00248 Torsten Irrgang 1 , Rhett Kempe 1
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The reductive amination, the reaction of an aldehyde or a ketone with ammonia or an amine in the presence of a reducing agent and often a catalyst, is an important amine synthesis and has been intensively investigated in academia and industry for a century. Besides aldehydes, ketones, or amines, starting materials have been used that can be converted into an aldehyde or ketone (for instance, carboxylic acids or organic carbonate or nitriles) or into an amine (for instance, a nitro compound) in the presence of the same reducing agent and catalyst. Mechanistically, the reaction starts with a condensation step during which the carbonyl compound reacts with ammonia or an amine, forming the corresponding imine followed by the reduction of the imine to the alkyl amine product. Many of these reduction steps require the presence of a catalyst to activate the reducing agent. The reductive amination is impressive with regard to the product scope since primary, secondary, and tertiary alkyl amines are accessible and hydrogen is the most attractive reducing agent, especially if large-scale product formation is an issue, since hydrogen is inexpensive and abundantly available. Alkyl amines are intensively produced and use fine and bulk chemicals. They are key functional groups in many pharmaceuticals, agro chemicals, or materials. In this review, we summarize the work published on reductive amination employing hydrogen as the reducing agent. No comprehensive review focusing on this subject has been published since 1948, albeit many interesting summaries dealing with one or the other aspect of reductive amination have appeared. Impressive progress in using catalysts based on earth-abundant metals, especially nanostructured heterogeneous catalysts, has been made during the early development of the field and in recent years.
中文翻译：
过渡金属催化的氢还原胺化反应。
还原胺化是醛或酮与氨或胺在还原剂（通常是催化剂）存在下的反应，是一种重要的胺合成方法，已经在学术界和工业界进行了深入研究，已有一个世纪的历史。除醛，酮或胺外，还使用了可以在以下条件下转化为醛或酮（例如羧酸或有机碳酸酯或腈）或胺（例如硝基化合物）的原料。相同的还原剂和催化剂。从机理上讲，反应从缩合步骤开始，在该步骤中羰基化合物与氨或胺反应，形成相应的亚胺，然后将亚胺还原为烷基胺产物。这些还原步骤中的许多步骤都需要催化剂的存在来活化还原剂。由于伯，仲和叔烷基胺是可及的，并且氢是最有吸引力的还原剂，特别是在大规模产物形成的问题上，因为氢价格便宜且可大量获得，因此还原胺化在产品范围方面令人印象深刻。烷基胺大量生产，并使用精细的和大量的化学品。它们是许多药品，农用化学品或材料中的关键官能团。在这篇综述中，我们总结了关于使用氢作为还原剂的还原胺化的工作。自1948年以来，没有针对该主题的全面评论发表过，尽管出现了许多有趣的关于还原胺化的一个或另一个方面的综述。
更新日期：2020-09-10
中文翻译：
过渡金属催化的氢还原胺化反应。
还原胺化是醛或酮与氨或胺在还原剂（通常是催化剂）存在下的反应，是一种重要的胺合成方法，已经在学术界和工业界进行了深入研究，已有一个世纪的历史。除醛，酮或胺外，还使用了可以在以下条件下转化为醛或酮（例如羧酸或有机碳酸酯或腈）或胺（例如硝基化合物）的原料。相同的还原剂和催化剂。从机理上讲，反应从缩合步骤开始，在该步骤中羰基化合物与氨或胺反应，形成相应的亚胺，然后将亚胺还原为烷基胺产物。这些还原步骤中的许多步骤都需要催化剂的存在来活化还原剂。由于伯，仲和叔烷基胺是可及的，并且氢是最有吸引力的还原剂，特别是在大规模产物形成的问题上，因为氢价格便宜且可大量获得，因此还原胺化在产品范围方面令人印象深刻。烷基胺大量生产，并使用精细的和大量的化学品。它们是许多药品，农用化学品或材料中的关键官能团。在这篇综述中，我们总结了关于使用氢作为还原剂的还原胺化的工作。自1948年以来，没有针对该主题的全面评论发表过，尽管出现了许多有趣的关于还原胺化的一个或另一个方面的综述。
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