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Synlett
DOI: 10.1055/a-2596-9970
letter
Hydrogen Atom Transfer Reactions

Zwitterionic Acridinium Amidate for Photocatalytic Acceptorless Dehydrogenation

Soichiro Mori‡
a   Institute of Transformative Bio-Molecules (WPI-ITbM), and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan
,
Lukas-Maximilian Entgelmeier‡
b   Organic Chemistry Institute, University of Münster, 48149 Münster, Germany
,
Yaoki Kansaku
a   Institute of Transformative Bio-Molecules (WPI-ITbM), and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan
,
Duc An Truong
a   Institute of Transformative Bio-Molecules (WPI-ITbM), and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan
,
Olga García Mancheño∗
b   Organic Chemistry Institute, University of Münster, 48149 Münster, Germany
,
Kohsuke Ohmatsu∗
c   Department of Chemistry, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan
,
Takashi Ooi∗
a   Institute of Transformative Bio-Molecules (WPI-ITbM), and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8601, Japan
› Institutsangaben
This work was financially supported by MEXT KAKENHI Grants JP23H04901 and JP23H04907 (Green Catalysis Science); JSPS KAKENHI Grants 24K01481, 23H00296, and 22K21346; and JST FOREST Grant JPMJFR221L. The Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) within the IRTG 2678–Functional π-Systems (pi-Sys) (Münster-Nagoya International Research Training Group, GRK 2678-437785492) and grant GA 1594-6/2 are also gratefully acknowledged for generous financial support.
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Abstract

The development of catalytic systems that facilitate simple yet valuable molecular transformations in a sustainable manner is of fundamental importance in the field of synthetic organic chemistry. Herein, we report the expedient application of a zwitterionic acridinium amidate, a recently developed direct hydrogen-atom-transfer catalyst, in catalytic acceptorless dehydrogenation (CAD). The combined use of the acridinium amidate with a cobaloxime complex and a protic additive as a catalyst system enables the CAD of hydrocarbons to proceed with high efficiency under mild reaction conditions.

Key word

acceptorless dehydrogenation - photocatalysis - zwitterions - hybrid catalysis - dehydrogenation - aromatization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2596-9970.
  • Supporting Information


Publikationsverlauf

Eingereicht: 11. März 2025

Angenommen nach Revision: 29. April 2025

Accepted Manuscript online:
29. April 2025

Artikel online veröffentlicht:
10. Juni 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

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