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Lookup NU author(s): Dr Matt HopkinsonORCiD
This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).
The combination of N-heterocyclic carbene (NHC) organocatalysis with photochemical activation is becoming increasingly established as an approach for conducting radical organic reactions under mild and practical conditions. As comparatively easy to prepare and handle organic compounds, alkyl silanes are attractive substrates for radical chemistry as desilylative mesolysis of the corresponding radical cations is known to be rapid. Here, we report the successful application of benzyl silane derivatives as source of alkyl radicals in dual NHC/photoredox-catalyzed radical-radical coupling reactions with acyl fluorides. Relatively electron-rich benzyl silanes reacted smoothly to afford the corresponding ketones in generally good yields, while optimization of the NHC and photocatalyst allowed for a wider scope including primary benzyl substrates. Furthermore, initial experiments revealed that organosilanes bearing N-, O- and S-heteroatoms can also serve as alkyl radical sources under these conditions.
Author(s): Jakob M, Steiner L, Göbel M, Götze JP, Hopkinson MN
Publication type: Article
Publication status: Published
Journal: ACS Catalysis
Year: 2024
Pages: Epub ahead of print
Online publication date: 15/11/2024
Acceptance date: 05/11/2024
Date deposited: 19/11/2024
ISSN (electronic): 2155-5435
Publisher: American Chemical Society
URL: https://doi.org/10.1021/acscatal.4c03103
DOI: 10.1021/acscatal.4c03103
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