Visible-Light-Driven Thioesterification of Aryl Halides with Potassium Thiocarboxylates: Transition-Metal Catalyst-Free Incorporation of Sulfur Functionalities into an Aromatic Ring

Reactions of acceptor-substituted aryl iodides and bromides with potassium thiocarboxylates under white light irradiation allow for the preparation of S-aryl thioesters including synthetically versatile S-aryl thioacetates. This transition-metal and external photocatalyst-free method features extrem...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-06, Vol.87 (12), p.8170-8182
Main Authors: Volkov, Alexey A., Bugaenko, Dmitry I., Bogdanov, Alexey V., Karchava, Alexander V.
Format: Article
Language:English
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Summary:Reactions of acceptor-substituted aryl iodides and bromides with potassium thiocarboxylates under white light irradiation allow for the preparation of S-aryl thioesters including synthetically versatile S-aryl thioacetates. This transition-metal and external photocatalyst-free method features extremely mild reaction conditions compared with those used in transition-metal-catalyzed protocols. Reactions proceed via the initial formation of an electron donor–acceptor (EDA) complex in the ground state, which was supported by UV–vis spectra. Electron paramagnetic resonance (EPR) spin-trapping experiments using phenyl-N-tert-butylnitrone (PBN) have revealed the radical nature of the reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00913