Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones

Schwengers, Sebastian Armin; Gerosa, Gabriela Guillermina; Amatov, Tynchtyk; Yasukawa, Naoki; Brunen, Sebastian; Leutzsch, Markus; Mitschke, Benjamin; Shevchenko, Grigory André; List, Benjamin

doi:10.1002/anie.202307081

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Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones

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Schwengers, Sebastian Armin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons230441

Gerosa, Gabriela Guillermina
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons242053

Amatov, Tynchtyk
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons290741

Yasukawa, Naoki
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons290597

Brunen, Sebastian
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons132873

Leutzsch, Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons251523

Mitschke, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons180743

Shevchenko, Grigory André
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58764

List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Schwengers, S. A., Gerosa, G. G., Amatov, T., Yasukawa, N., Brunen, S., Leutzsch, M., et al. (2023). Direct Regioselective Dehydrogenation of α-Substituted Cyclic Ketones. Angewandte Chemie International Edition, 62(35): e202307081. doi:10.1002/anie.202307081.

Cite as: https://hdl.handle.net/21.11116/0000-000D-666A-A

Abstract

We disclose a highly regioselective, catalytic one-step dehydrogenation of α-substituted cyclic ketones in the presence of 2,3-dichlorobenzo-5,6-dicyano-1,4-benzoquinone (DDQ). The high regioselectivity originates from a phosphoric acid-catalyzed enolization, selectively affording the thermodynamically preferred enol, followed by the subsequent oxidation event. Our method provides reliable access to several α-aryl and α-alkyl substituted α,β-unsaturated ketones.