Diversity-Orientated Stereoselective Synthesis through Pd- Catalyzed Switchable Decarboxylative C‒N/C‒S Bond Formation in Allylic Surrogates
Switchable catalytic transformation of reactants can be a powerful approach towards diversity-orientated synthesis from easily available molecular synthons. Herein, an endogenous ligand- controlled, Pd-catalyzed allylic substitution allowing for either selective C‒N or C‒S bond formation using vinyl...
| Autores: | , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2018 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/356172 |
| Acceso en línea: | http://hdl.handle.net/2072/356172 https://doi.org/10.1002/chem.201805295 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | Switchable catalytic transformation of reactants can be a powerful approach towards diversity-orientated synthesis from easily available molecular synthons. Herein, an endogenous ligand- controlled, Pd-catalyzed allylic substitution allowing for either selective C‒N or C‒S bond formation using vinylethylene carbonates and N-sulfonylhydrazones as coupling partners has been developed. This versatile methodology provides a facile, diversicating route for the highly chemo- and stereoselective synthesis of functional allylic sulfones or sulfonohydrazides. The newly developed protocol features wide substrate scope (nearly 80 examples), broad functional group tolerance and potential for the late-stage functionalization of bioactive compounds. The isolation and crystallographic analysis of a catalytically competent -allyl Pd complex suggests that the pathway leading to the allylic products proceeds through a different manifold as previously proposed for the functionalization of VECs with nucleophiles. |
|---|