{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,11]],"date-time":"2025-11-11T13:38:49Z","timestamp":1762868329964,"version":"build-2065373602"},"reference-count":45,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2020,11,23]],"date-time":"2020-11-23T00:00:00Z","timestamp":1606089600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UIDB\/00100\/2020","CO2usE-1801P.00867.1.01"],"award-info":[{"award-number":["UIDB\/00100\/2020","CO2usE-1801P.00867.1.01"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"NCN program","award":["2012\/07\/B\/ST\/00885"],"award-info":[{"award-number":["2012\/07\/B\/ST\/00885"]}]},{"DOI":"10.13039\/501100007225","name":"Instituto Superior T\u00e9cnico","doi-asserted-by":"publisher","award":["IST-ID\/263\/2019"],"award-info":[{"award-number":["IST-ID\/263\/2019"]}],"id":[{"id":"10.13039\/501100007225","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u20133 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 \u2018click rules\u2019.<\/jats:p>","DOI":"10.3390\/molecules25225479","type":"journal-article","created":{"date-parts":[[2020,11,23]],"date-time":"2020-11-23T11:50:34Z","timestamp":1606132234000},"page":"5479","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8212-2102","authenticated-orcid":false,"given":"Abdallah","family":"Mahmoud","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Science, Helwan University, Ain Helwan, 11795 Cairo, Egypt"},{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa Av. Rovisco Pais, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5969-6012","authenticated-orcid":false,"given":"Piotr","family":"Smole\u0144ski","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, Ul. F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4836-2409","authenticated-orcid":false,"given":"M.","family":"Guedes da Silva","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa Av. Rovisco Pais, 1049-001 Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8323-888X","authenticated-orcid":false,"given":"Armando","family":"Pombeiro","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Instituto Superior T\u00e9cnico, Universidade de Lisboa Av. Rovisco Pais, 1049-001 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2020,11,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1039\/b418069k","article-title":"Green solvents for sustainable organic synthesis: State of the art","volume":"7","author":"Sheldon","year":"2005","journal-title":"Green Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"927","DOI":"10.1039\/b617536h","article-title":"What is a green solvent? A comprehensive framework for the environmental assessment of solvents","volume":"9","author":"Capello","year":"2007","journal-title":"Green Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1021\/cr800403r","article-title":"Hydrophilic ligands and their application in aqueous-phase metal-catalyzed reactions","volume":"109","author":"Shaughnessy","year":"2009","journal-title":"Chem. 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