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Site‐Selective C−H Oxygenation via Aryl Sulfonium Salts

Herein, we report a two‐step process forming arene C−O bonds in excellent site‐selectivity at a late‐stage. The C−O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C−O bonds using photoredox chemistry. Electron‐rich, ‐poor and ‐neutral aren...

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Detalles Bibliográficos
Autores principales: Sang, Ruocheng, Korkis, Stamatis E., Su, Wanqi, Ye, Fei, Engl, Pascal S., Berger, Florian, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7754133/
https://www.ncbi.nlm.nih.gov/pubmed/31475767
http://dx.doi.org/10.1002/anie.201908718
Descripción
Sumario:Herein, we report a two‐step process forming arene C−O bonds in excellent site‐selectivity at a late‐stage. The C−O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C−O bonds using photoredox chemistry. Electron‐rich, ‐poor and ‐neutral arenes as well as complex drug‐like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in that oxygen functionality can be incorporated into complex small molecules at a late stage site‐selectively, which has not been shown via aryl halides.