One-pot Iron(III) /Cationic 2,2'-Bipyridyl System Catalyzed Sonogashira-Hagihara Coupling in Water
| Autor: | Tzu-Ting Hung, 洪慈婷 |
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| Rok vydání: | 2010 |
| Druh dokumentu: | 學位論文 ; thesis |
| Popis: | 98 The cross-coupling between an aryl halide and terminal alkyne catalyzed by palladium catalyst is widely known as the Sonogashira-Hagihara reaction. It provides a powerful method for the preparation of aryl alkynes which are important compounds for material sciences and medicinal chemistry. In the past decade, an effort was made to develop efficient catalytic systems by using cheap transition metals, such as copper or nickel catalysts and with adequate ligands. Recently, the Sonogashira-Hagihara reaction was developed on iron-catalyed because iron is the cheapest transition metal, non-toxic, and environmentally benign. However, such reactions still use organic solvents as reaction medium. Here we report a green process using FeCl3．6H2O as a catalyst in the cleanest solvent, water, for Sonogashira-Hagihara reaction. We introduced a water-soluble cationic 2,2´-bipyridyl ligand to bring the catalyst into aqueous phase enabled the reaction of aryl iodies with terminal alkynes and 1-aryl-3-methyl-1-butyn-3-ol to form diaryl alkynes in water under air in good to excellent yields. Specially, terminal alkynes can be generated in situ from 1-aryl-3-methyl-1-butyn -3-ol. This procedure reduced the wastage of organic solvents for the isolation of terminal alkynes. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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