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Journal Article

Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles

MPS-Authors
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Chen,  Junting
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Plutschack,  Matthew B.
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

Chen, J., Li, J., Plutschack, M. B., Berger, F., & Ritter, T. (2020). Regio‐ and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles. Angewandte Chemie, International Edition, 59(14), 5616-5620. doi:10.1002/anie.201914215.


Cite as: https://hdl.handle.net/21.11116/0000-0005-EEE5-D
Abstract
Herein, we report a regioselective alkenyl electrophile synthesis from unactivated olefins that is based on a direct and regioselective C−H thianthrenation reaction. The selectivity is proposed to arise from an unusual inverse‐electron‐demand hetero‐Diels–Alder reaction. The alkenyl sulfonium salts can serve as electrophiles in palladium‐ and ruthenium‐catalyzed cross‐coupling reactions to make alkenyl C−C, C−Cl, C−Br, and C−SCF3 bonds with stereoretention.