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

Alexey A. Volkov, Dmitry I. Bugaenko*, Alexey V. Bogdanov, Alexander V. Karchava*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8170-8182
Number of pages13
JournalJournal of Organic Chemistry
Volume87
Issue number12
DOIs
Publication statusPublished - 17 Jun 2022
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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