Visible light-mediated cyclisation reaction for the synthesis of highly-substituted tetrahydroquinolines and quinolines
Abstract
Condensation of 2-vinylanilines and conjugated aldehydes followed by an efficient light-mediated cyclisation selectively yields either substituted tetrahydroquinolines with typically high dr, or in the presence of an iridium photocatalyst the synthesis of quinoline derivatives is demonstrated. These atom economical processes require mild conditions, with the substrate scope demonstrating excellent site selectivity and functional group tolerance, including azaarene-bearing substrates. A thorough experimental mechanistic investigation explores multiple pathways and the key role that imine and iminium intermediates play in the absorption of visible light to generate reactive excited states. The synthetic utility of the reactions is demonstrated on gram scale quantities in both batch and flow, alongside further manipulation of the medicinally relevant products.
Citation
Sherborne , G J , Kemmitt , P , Prentice , C , Zysman-Colman , E , Smith , A D & Fallan , C 2023 , ' Visible light-mediated cyclisation reaction for the synthesis of highly-substituted tetrahydroquinolines and quinolines ' , Angewandte Chemie International Edition , vol. 62 , no. 2 , e202207829 . https://doi.org/10.1002/anie.202207829
Publication
Angewandte Chemie International Edition
Status
Peer reviewed
ISSN
1433-7851Type
Journal article
Description
Funding: CP thanks AstraZeneca for funding.Collections
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