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

• Published in: Molecules (Basel, Switzerland) Switzerland), 2020-11, Vol.25 (22), p.5479
• Main Authors: Mahmoud, Abdallah G, Smoleński, Piotr, Guedes da Silva, M Fátima C, Pombeiro, Armando J L
• Format: Article
• Language: English
• Subjects: Acetic acid; Alkynes; Alkynes - chemistry; Aqueous solutions; Azides - chemistry; Catalysis; Catalysts; Chemistry Techniques, Synthetic; click chemistry; Copper; Copper compounds; CuAAC; Cycloaddition; Cycloaddition Reaction; DAPTA; Diacetyl; Environmental impact; Geometry; homogeneous catalysis; Ligands; Magnetic Resonance Spectroscopy; Molecular Structure; NMR; NMR spectroscopy; Nuclear magnetic resonance; Organic solvents; Oxygen - chemistry; P ligands; Phosphines - chemical synthesis; Phosphines - chemistry; Phosphorus; Selenium - chemistry; Single crystals; Solubility; Solvents; Sulfides; Sulfides - chemistry; Triazoles; Triazoles - chemistry; water-soluble ligands; X-Ray Diffraction
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules25225479

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, ), the novel 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-sulfide (DAPTA=S, ), and 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-selenide (DAPTA=Se, ), have been synthesized under mild conditions. They are soluble in water and most common organic solvents and have been characterized using H and P NMR spectroscopy and, for and , 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 - 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 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'.