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Stable homogeneous silver(I) catalysts for the highly efficient cycloaddition of azides onto terminal alkynes in water
Dalton Transactions ( IF 3.5 ) Pub Date : 2024-11-11 , DOI: 10.1039/d4dt02825b
Meysam Kakavand, Anna Kozakiewicz-Piekarz, Abdollah Neshat

To develop stable and efficient silver(I) catalysts and evaluate the role of sulfur and phosphorus donor ligands in the catalytic cycloaddition of selected organic azides and alkynes (AAC), a series of mononuclear Ag(I) and heteronuclear Ag(I)–Fe(II) complexes were synthesized. The synthesis utilized phosphine and sulfur donors from the dialkyldithiophosphate and borate families, specifically Na[S2H2B(mt)2]. These complexes are designated as [(dppf)AgSP(S)(OiPr)2] (1), [S2H2B(mt)2Ag(μ-dppf)AgS2H2B(mt)2] (2), [(dppf)Ag(μ-dppf)Ag(dppf)] (3), and [(dppe)AgS2H2B(mt)2] (5). The complexes 1–5 were characterized using a combination of 1H, 13C{1H}, and 31P{1H} NMR spectroscopy, as well as IR spectroscopy techniques. In two instances, single-crystal X-ray diffraction analysis was also employed. Complex 3 exhibited high catalytic activity and regioselectivity in the cycloaddition reaction conducted in water at 40 °C.

中文翻译:


稳定的均相银 (I) 催化剂,用于将叠氮化物高效地环加成到水中的末端炔烃上



为了开发稳定高效的银()催化剂并评价硫和磷供体配体在选定的有机叠氮化物和炔烃(AAC)的催化环加成反应中的作用,合成了一系列单核Ag()和异核Ag()-Fe(II)配合物。该合成利用了来自二烷基二硫代磷酸酯和硼酸盐家族的磷化氢和硫供体,特别是 Na[S2H2B(mt)2]。这些配合物被命名为 [(dppf)AgSP(S)(OPr)2] (1)、[S2H2B(mt)2Ag(μ-dppf)AgS2H2B(mt)2] (2)、[(dppf)Ag(μ-dppf)Ag(dppf)] (3) 和 [(dppe)AgS2H2B(mt)2] (5)。使用 1H、13C{1H} 和 31P{1H} NMR 波谱以及红外光谱技术的组合对复合物 1-5 进行表征。在两个实例中,还采用了单晶 X 射线衍射分析。复合物 3 在 40 °C 水中进行的环加成反应中表现出高催化活性和区域选择性。
更新日期:2024-11-14
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