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A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOF3 Compounds
1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, Mülheim an der Ruhr, 45470, Germany.
This study introduces a new method to create diverse aryl sulfur(VI) fluorides from aryl halides. The process allows for selective fluorination, yielding valuable compounds like aryl-SOF3, useful in synthesizing other complex molecules.
Area of Science:
- Organic Chemistry
- Fluorine Chemistry
- Sulfur Chemistry
Background:
- Aryl sulfur(VI) fluorides are important synthetic intermediates.
- Selective synthesis of diverse sulfur(VI) fluorides remains challenging.
Purpose of the Study:
- To develop a divergent protocol for accessing various arylsulfur(VI) fluorides.
- To enable the introduction of the rare aryl-SOF3 moiety.
- To explore the synthetic utility of aryl-SOF3 compounds.
Main Methods:
- Sulfenylation of aryl halides using N-(chlorothio)phthalimide and arylzinc reagents.
- Selective oxidation of S(II) to S(VI) under mild conditions.
- Chemoselective installation of 1, 3, or 4 fluorine atoms.
Main Results:
- A novel protocol provides access to Ar-S-Phth, Ar-SO2F, Ar-SOF3, and Ar-SF4Cl.
- The method effectively introduces the underexplored Ar-SOF3 group.
- Ar-SOF3 compounds serve as precursors for aryl sulfonimidoyl fluorides.
Conclusions:
- A versatile and convenient method for synthesizing arylsulfur(VI) fluorides is established.
- The protocol offers control over fluorination levels and moiety introduction.
- The developed Ar-SOF3 intermediates open new synthetic pathways.
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