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Recent Developments in the Reduction of Aromatic and Aliphatic Nitro Compounds to Amines
Organic Process Research & Development ( IF 3.4 ) Pub Date : 2016-07-21 00:00:00 , DOI: 10.1021/acs.oprd.6b00205
Manuel Orlandi 1 , Davide Brenna 1 , Reentje Harms 2 , Sonja Jost 2 , Maurizio Benaglia 1
Affiliation  

The reduction of the nitro group represents a powerful and widely used transformation that allows to introducing an amino group in the molecule. New synthetic strategies for complex functionalized molecular architectures are deeply needed, including highly efficient and selective nitro reduction methods, tolerant of a diverse array of functional moieties and protecting groups. Since chiral amino groups are ubiquitous in a variety of bioactive molecules such as alkaloids, natural products, drugs, and medical agents, the development of reliable catalytic methodologies for the nitro group reduction is attracting an increasing interest also in the preparation of enantiomerically pure amines. In this context, the modern reduction methods should be chemoselective and respectful of the stereochemical integrity of the stereogenic elements of the molecule. The review will offer an overview of the different possible methodologies available for this fundamental transformation, with special attention on the most recent contributions in the field, especially in the last ten years: hydrogenations, metal dissolving and hydride transfer reductions, catalytic transfer hydrogenations, and metal-free reductions. The main advantages or limitations for the proposed methods will be briefly discussed, highlighting in some cases the most important features of the presented reduction methodologies from an industrial point of view.

中文翻译:

芳香族和脂肪族硝基化合物还原为胺的最新进展

硝基的还原代表了强大且广泛使用的转化,其允许在分子中引入氨基。迫切需要用于复杂功能化分子结构的新合成策略,包括高效和选择性的硝基还原方法,耐受各种各样的功能部分和保护基团。由于手性氨基在各种生物活性分子(如生物碱,天然产物,药物和药物)中无处不在,因此开发可靠的硝基还原催化方法在对映体纯胺的制备中也引起了越来越多的兴趣。在这种情况下,现代还原方法应该是化学选择性的,并且要尊重分子的立体成因元素的立体化学完整性。这篇综述将概述可用于这一基本转变的各种不同方法,特别关注该领域的最新贡献,尤其是最近十年:氢化,金属溶解和氢化物转移减少,催化转移氢化以及无金属的减少。将简要讨论所提出方法的主要优点或局限性,在某些情况下,从工业角度强调所提出的还原方法的最重要特征。催化转移氢化和无金属还原。将简要讨论所提出方法的主要优点或局限性,在某些情况下,从工业角度强调所提出的还原方法的最重要特征。催化转移氢化和无金属还原。将简要讨论所提出方法的主要优点或局限性,在某些情况下,从工业角度强调所提出的还原方法的最重要特征。
更新日期:2016-07-21
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