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Synthesis of triazolyl-alkylphosphonate starting from ω-azidoalkylphosphonates or ω-alkynylphosphonates |
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| Authors: | Lise Delain-Bioton Jean-François Lohier Paul-Alain Jaffrès |
| Institution: | a LCMT, UMR CNRS 6507, Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 Bd du Maréchal Juin, F-14050 Caen, France b Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen, 5 rue Vaubénard, F-14032 Caen, France c CEMCA, UMR CNRS 6521, Faculté des Sciences et Techniques, Université de Bretagne Occidentale, 6 avenue Le Gorgeu, F-29238 Brest, France |
| Abstract: | 1,2,3-Triazolyl-alkylphosphonates are synthesised according to a Huisgen 1,3-dipolar cycloaddition catalysed by copper salts. The cycloaddition of either an alkynylphosphonate with an azidoalkane or an azido-phosphonate with an alkyne is achieved in high yield and regiospecifically. As an illustration of the functionalisation of aromatic ligands by using the catalytic version of the Huisgen reaction, the coupling of 3-ethynyl-1,10-phenanthroline with azidoalkylphosphonate is reported. |
| Keywords: | Phosphonate Azide Alkyne Huisgen reaction |
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