Issue 19, 2024

Transition metal-free synthesis of polyfluoroaryl sulfides via S-transfer reaction

Abstract

We report herein an efficient, transition metal-free protocol for synthesizing polyfluoroaryl sulfides using cheap and odorless sulfur reagents, specifically thiourea and potassium thioacetate. A key advancement in this method is the identification of thioamides as effective S-transfer reagents, which react with polyfluoroarenes to form symmetrical polyfluorodiaryl sulfides. Following extensive optimization, the protocol demonstrates significant robustness, flexibility, and compatibility with a broad array of functional groups. Additionally, commercially available alkyl bromides and arynes can serve as secondary electrophiles, coupling with polyfluoroarene-substituted sulfur anion intermediates to produce unsymmetrical polyfluoroaryl sulfides. The practicality of the method is further investigated by its facile gram-scale synthesis, diverse synthetic applications, and potential for late-stage functionalization, highlighting its utility in advancing aryl sulfide and fluorine chemistry. Mechanistic insights were elucidated through crossover, control, and radical inhibition experiments.

Graphical abstract: Transition metal-free synthesis of polyfluoroaryl sulfides via S-transfer reaction

Supplementary files

Article information

Article type
Research Article
Submitted
11 Jul 2024
Accepted
14 Aug 2024
First published
16 Aug 2024

Org. Chem. Front., 2024,11, 5558-5563

Transition metal-free synthesis of polyfluoroaryl sulfides via S-transfer reaction

Y. Wang, M. Liu, H. Zhou, T. Qin, B. Liu and X. Lu, Org. Chem. Front., 2024, 11, 5558 DOI: 10.1039/D4QO01276C

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