Subnanometer Gold Clusters on Amino-Functionalized Silica: An Efficient Catalyst for the Synthesis of 1,3-Diynes by Oxidative Alkyne Coupling
| Autor: | Antonio Togni, Beáta Vilhanová, Luca Artiglia, Jeroen A. van Bokhoven, Jiří Václavík, Marco Ranocchiari |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Hypervalent molecule Alkyne General Chemistry 010402 general chemistry Heterogeneous catalysis Photochemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Amino functionalized Coupling (electronics) chemistry.chemical_compound chemistry Organic synthesis Efficient catalyst |
| Zdroj: | ACS Catalysis. 7:3414-3418 |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.7b00691 |
| Popis: | Subnanometer (d = 0.8 ± 0.2 nm) gold particles homogeneously dispersed on amino-functionalized silica catalyze Glaser-type alkyne coupling, providing corresponding 1,3-diynes under mild conditions. Readily available λ3-iodane PhI(OAc)2 is used as an oxidant and 1,10-phenanthroline is used as an additive. Ten symmetrical 1,3-diynes and three products of heterocoupling containing various functionalities are isolated in high yields. The catalyst can be recycled at least five times, giving consistently high isolated yields and maintaining the size and distribution of gold clusters. This unique combination of stable subnanometer gold clusters and hypervalent iodine thus paves a hitherto unexplored avenue in organic synthesis employing heterogeneous gold catalysis. |
| Databáze: | OpenAIRE |
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