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银催化一锅三组分合成α-氨基腈及与生物相关的α-氨基膦酸酯

Silver-Catalyzed One-Pot Three-Component Synthesis of α-Aminonitriles and Biologically Relevant α-Amino-phosphonates.

作者信息

Pandey Vipin K, Tiwari Chandra Shekhar, Rit Arnab

机构信息

Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.

出版信息

Chem Asian J. 2022 Oct 17;17(20):e202200703. doi: 10.1002/asia.202200703. Epub 2022 Sep 8.

Abstract

A simple silver salt (AgSbF )-catalyzed aminophosphonylation and Strecker reaction have been developed and successfully applied to a wide range of substrates (>55 substrates). This solvent-, ligand-, and base-free one-pot three-component protocol operates effectively at room temperature to provide diversified α-aminophosphonates and α-aminonitriles, which gave access to the respective α-amino amides. Importantly, the present catalyst system is also capable to produce the rarely reported and biologically relevant aminophosphonates (having anti-leishmanial activity). Further, mechanistic studies reveal that the present phosphonylation protocol follows a radical pathway.

摘要

已开发出一种简单的银盐(AgSbF)催化的氨基膦酰化反应和斯特雷克反应,并成功应用于多种底物(>55种底物)。这种无溶剂、无配体和无碱的一锅三组分方法在室温下有效运行,可提供多种α-氨基膦酸酯和α-氨基腈,进而可得到相应的α-氨基酰胺。重要的是,目前的催化剂体系还能够制备很少报道且具有生物学相关性的氨基膦酸酯(具有抗利什曼原虫活性)。此外,机理研究表明,目前的膦酰化反应遵循自由基途径。

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