Photochemical Organocatalytic Benzylation of Allylic C-H Bonds
We report a radical-based organocatalytic method for the direct benzylation of allylic C-H bonds. The process uses non-functionalized allylic substrates and readily available benzyl radical precursors and is driven by visible light. Crucial was the identification of a dithiophosphoric acid that perf...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2022 |
| 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:2072/521033 |
| Acceso en línea: | http://hdl.handle.net/2072/521033 https://doi.org/10.1021/jacs.1c11712 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | We report a radical-based organocatalytic method for the direct benzylation of allylic C-H bonds. The process uses non-functionalized allylic substrates and readily available benzyl radical precursors and is driven by visible light. Crucial was the identification of a dithiophosphoric acid that performs two distinct catalytic roles, sequentially acting as a catalytic donor for the formation of photoactive electron donor-acceptor (EDA) complexes and then as a hydrogen atom abstractor. By mastering these orthogonal radical generation paths, the organic catalyst enables the formation of benzylic and allylic radicals, respectively, to then govern their selective coupling. The protocol was also used to design a three-component radical process, which increased the synthetic potential of the chemistry. |
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