A Domino Process towards Functionally Dense Quaternary Carbons through Pd-Catalyzed Decarboxylative Csp3-Csp3 Bond Formation
An efficient protocol was developed to construct functionally dense quaternary carbons with concomitant formation of a new Csp3-Csp3 bond via Pd-catalyzed decarboxylative transformation of vinyl cyclic carbonates. This redox neutral catalytic system features stereocontrolled formation of multi-subst...
| Autores: | , , , , |
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| 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:2072/356262 |
| Acceso en línea: | http://hdl.handle.net/2072/356262 https://doi.org/10.1021/jacs.7b12608 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | An efficient protocol was developed to construct functionally dense quaternary carbons with concomitant formation of a new Csp3-Csp3 bond via Pd-catalyzed decarboxylative transformation of vinyl cyclic carbonates. This redox neutral catalytic system features stereocontrolled formation of multi-substituted allylic scaffolds with an aldehyde functionality generated in situ, and it typically can be performed at room temperature without any additives. DFT calculations provide a rationale towards the selective formation of these compounds, and revealed a complex mechanism that is able to reproduce with the help of microkinetic models the non-trivial dependence between the identity of the product and the nature of the substituents in the substrate. |
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