Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

Molecules

Armando J. L. Pombeiro¹  M. Fátima C. Guedes da Silva¹  Abdallah G. Mahmoud²  Piotr Smoleński³ 

[1] Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa Av. Rovisco Pais, 1049-001 Lisboa, Portugal;Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan, 11795 Cairo, Egypt;Faculty of Chemistry, University of Wrocław, Ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland;

关键词: P ligands;    water-soluble ligands;    homogeneous catalysis;    click chemistry;    DAPTA;    CuAAC;   

DOI  :  10.3390/molecules25225479

来源: DOAJ

【 摘 要 】

The 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) derivatives, viz. the already reported 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane 5-oxide (DAPTA=O, 1), the novel 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-sulfide (DAPTA=S, 2), and 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-selenide (DAPTA=Se, 3), have been synthesized under mild conditions. They are soluble in water and most common organic solvents and have been characterized using ¹H and ³¹P NMR spectroscopy and, for 2 and 3, also by single crystal X-ray diffraction. The effect of O, S, or Se at the phosphorus atom on the structural features of the compounds has been investigated, also through the analyses of Hirshfeld surfaces. The presence of 1–3 enhances the activity of copper for the catalytic azide-alkyne cycloaddition reaction in an aqueous medium. The combination of cheaply available copper (II) acetate and compound 1 has been used as a catalyst for the one-pot and 1,4-regioselective procedure to obtain 1,2,3-triazoles with high yields and according to ‘click rules’.

【 授权许可】

Unknown