A metal-free synthesis of phosphoramidates via I^--catalyzed oxidative coupling of anilines/amines with H-phosphonates.

IF 3.8 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2025-08-23 DOI:10.1007/s11030-025-11327-y

Mengyu Xie, Huiting Xu, Linjiao Zhu, Tao Cai, Runpu Shen

引用次数: 0

Abstract

An efficient and environmentally benign protocol for synthesizing valuable and structurally diverse phosphoramidates via the sodium iodide (NaI)-catalyzed oxidative cross-coupling of various H-phosphonates with both aromatic and aliphatic amines. This new method utilizes H₂O₂ (30% aq.) as a green oxidant, ethyl acetate (EA) as a renewable, low-toxic solvent, and inexpensive, readily available NaI (10 mol%) as the sole catalyst, circumventing the need for toxic reagents, transition metal catalysts, and special equipment. It exhibits excellent compatibility with a wide range of aromatic and aliphatic amines, as well as several amino-containing pharmaceuticals, including Vortioxetine, Fluoxetine, Ceritinib, Linagliptin, and Crizotinib.

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苯胺/胺与h -膦酸盐通过I催化氧化偶联无金属合成磷酸酯。

通过碘化钠（NaI）催化各种h -膦酸盐与芳香胺和脂肪胺的氧化交叉偶联，合成有价值且结构多样的磷酰胺的高效和环保方案。这种新方法利用H2O2 （30% aq）作为绿色氧化剂，乙酸乙酯（EA）作为可再生的低毒溶剂，以及廉价易得的NaI （10 mol%）作为唯一催化剂，避免了对有毒试剂、过渡金属催化剂和特殊设备的需要。它与广泛的芳香族和脂肪族胺以及几种含氨基药物，包括沃替西汀、氟西汀、西瑞替尼、利格列汀和克唑替尼具有良好的相容性。

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

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;

A metal-free synthesis of phosphoramidates via I--catalyzed oxidative coupling of anilines/amines with H-phosphonates.

Abstract

A metal-free synthesis of phosphoramidates via I^--catalyzed oxidative coupling of anilines/amines with H-phosphonates.