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Journal Article

Site‐selective C−H Oxygenation via Aryl Sulfonium Salts

MPS-Authors
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Sang,  Ruocheng
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Korkis,  Stamatis E.
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Su,  Wanqi
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ye,  Fei
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Engl,  Pascal S.
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Berger,  Florian
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Ritter,  Tobias
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Sang, R., Korkis, S. E., Su, W., Ye, F., Engl, P. S., Berger, F., et al. (2019). Site‐selective C−H Oxygenation via Aryl Sulfonium Salts. Angewandte Chemie, International Edition, 58(45), 16161-16166. doi:10.1002/anie.201908718.


Cite as: https://hdl.handle.net/21.11116/0000-0004-F0C6-D
Abstract
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.