Dealuminated H-Y zeolites generate, stabilize and catalytically insert carbenes from diazocarbonyl compounds
[EN] Carbenes are among the most powerful reactants in organic synthesis, with capacity to insert into a variety of otherwise stable bonds, and generate two new bonds in a straightforward manner. However, the intrinsic instability of such carbenes makes them to be catalytically generated, in-situ, f...
| Authors: | , , , |
|---|---|
| Format: | article |
| Publication Date: | 2024 |
| Country: | España |
| Institution: | Universitat Politècnica de València (UPV) |
| Repository: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia |
| Language: | English |
| OAI Identifier: | oai:riunet.upv.es:10251/213371 |
| Online Access: | https://riunet.upv.es/handle/10251/213371 |
| Access Level: | Open access |
| Keyword: | Carbene insertion reactions Diazocarbonyl compounds Dealuminated H-Y zeolite Heterogeneous catalysis Solid Bronsted acid Reusable catalyst Organic synthesis Alkene cyclopropanation Buchner reaction Dioxygen insertion reaction |
| Summary: | [EN] Carbenes are among the most powerful reactants in organic synthesis, with capacity to insert into a variety of otherwise stable bonds, and generate two new bonds in a straightforward manner. However, the intrinsic instability of such carbenes makes them to be catalytically generated, in-situ, from precursors such as diazocarbonyl compounds, and the catalyst, in turn, also controls the subsequent insertion reaction. The catalyst is generally a metal complex in solution, mainly Cu, Ag or Rh, but also others, including protons in rare cases. Here we show that carbenes are generated, stabilized and inserted into C-C, C-H, O-H, N-H, Si-H and O-O bonds after reacting diazocarbonyl compounds with catalytic amounts of metal-free, commercially available dealuminated H-Y zeolites. These results open the way to design carbene-mediated organic reactions on readily available and reusable catalytic solids without involving metals. |
|---|