Novel Oxidative Ugi Reaction for the Synthesis of Highly Active, Visible‐Light, Imide‐Acridinium Organophotocatalysts

A newly designed class of acridinium‐based organophotocatalysts bearing an imide group at the C9‐position is presented. To achieve these unprecedented structures, a synthetic strategy based on a novel straightforward oxidative Ugi‐type reaction at the benzylic position of C9‐unsubstituted acridanes...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-08, Vol.24 (48), p.12509-12514
Main Authors: Gini, Andrea, Uygur, Mustafa, Rigotti, Thomas, Alemán, José, García Mancheño, Olga
Format: Article
Language:English
Subjects:
acridinium salts
Catalysis
Catalytic activity
Chemical synthesis
Chemistry
C−H functionalization
multicomponent reactions
oxidation
Photocatalysis
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Summary:A newly designed class of acridinium‐based organophotocatalysts bearing an imide group at the C9‐position is presented. To achieve these unprecedented structures, a synthetic strategy based on a novel straightforward oxidative Ugi‐type reaction at the benzylic position of C9‐unsubstituted acridanes was developed. The introduction of the imide‐unit affords a notable photocatalytic activity enhancement, allowing efficient transformations in different oxidative and reductive visible‐light catalytic reactions. Sweet′n′salty: The first, mild, modular, oxidative Ugi reaction on benzylic substrates, such acridanes, allows the development of an unprecedented family of imide‐acridinium visible‐light photocatalysts with boosted reactivities in both oxidative and reductive processes.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201802830