Streamlined Synthesis of Aminoacridinium Photocatalysts with Improved Photostability

Jakobi, Markus and Sparr, Christof. (2022) Streamlined Synthesis of Aminoacridinium Photocatalysts with Improved Photostability. Organic process research & development, 26 (9). pp. 2756-2760.

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Official URL: https://edoc.unibas.ch/91103/

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The efficient synthesis of photocatalysts with improved photostability from readily available resources is a requirement for more sustainable and scalable photocatalysis. Herein, we describe a strategy utilizing a high-yielding threefold C–N cross-coupling selective for three out of six arylbromide sites to avoid alkyl groups in the final catalyst structure. A subsequent triple metalation to form 1,5,5′-trifunctional organometallic reagents enables the coupling and cyclization with simple esters, whereas a third unreacted functionality is hydrolyzed upon acidic quench. This short reaction sequence results in bis(diarylamino)acridiniums with dramatically increased photostability, allowing us to lower the catalyst loading to 0.10 mol % without loss in yield.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr)
UniBasel Contributors:Sparr, Christof
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
Note:Publication type according to Uni Basel Research Database: Journal article
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edoc DOI:
Last Modified:31 Aug 2023 01:30
Deposited On:14 Dec 2022 08:43

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