Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ<sup>6</sup>-sulfanes to tetrafluoroethylene

Yasuo, Eisuke; Aikawa, Kohsuke; Nozaki, Kyoko; Okazoe, Takashi

doi:10.1039/d3sc04837c

Chem. Sci.

2023

DOI: 10.1039/d3sc04837c

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Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ⁶-sulfanes to tetrafluoroethylene

Eisuke Yasuo,

Kohsuke Aikawa,

Kyoko Nozaki

et al.

Abstract: Fluorinated groups are essential hydrophobic groups in drug design. Combining a carbon-free tetrafluoro-λ6-sulfanyl (SF4) group with a polyfluoroalkyl group (RF) provides SF4RF groups, exhibiting high hydrophobicity with a short carbon...

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Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups

Liu,

Okazoe,

Gatzenmeier

et al. 2024

ChemistryEurope

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Sulfur‐containing functional groups (SFGs) are increasingly important for modern medicinal chemistry and their large structural diversity provides many opportunities for lead optimization. In an effort to simplify the access to the full set of SFGs, we report herein a versatile strategy utilizing (hetero)aryl trityl sulfides (ArSCPh3) as the common precursors. We developed a mild and high yielding Pd‐catalyzed thiotritylation cross‐coupling methodology to afford ArSCPh3 compounds from (hetero)aryl bromides and iodides. Efficient chemoselective derivatizations provided access to eight different SFGs and sulfur(VI) fluorine exchange (SuFEx) hubs, which open up further downstream derivatizations towards the full set of SFGs. Thereby obtainable sulfur motifs include aryl sulfur pentafluorides (ArSF5), aryl tetrafluoro‐λ6‐sulfanyl chlorides (ArSF4Cl), aryl sulfonimidoyl fluorides (ArS(O)(NR)F), aryl sulfonyl fluorides (ArSO2F), aryl sulfonic acids (ArSO3H), and aryl sulfinyl fluorides (ArSOF), which are all valuable functional groups in modern drug discovery.

show abstract

Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups

Liu,

Okazoe,

Gatzenmeier

et al. 2024

ChemistryEurope

View full text Add to dashboard Cite

show abstract

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Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ⁶-sulfanes to tetrafluoroethylene

Abstract: Fluorinated groups are essential hydrophobic groups in drug design. Combining a carbon-free tetrafluoro-λ6-sulfanyl (SF4) group with a polyfluoroalkyl group (RF) provides SF4RF groups, exhibiting high hydrophobicity with a short carbon...

Cited by 1 publication

References 69 publications

Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups

Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups

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Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ6-sulfanes to tetrafluoroethylene

Abstract: Fluorinated groups are essential hydrophobic groups in drug design. Combining a carbon-free tetrafluoro-λ6-sulfanyl (SF4) group with a polyfluoroalkyl group (RF) provides SF4RF groups, exhibiting high hydrophobicity with a short carbon...

Cited by 1 publication

References 69 publications

Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups

Pd‐Catalyzed Thiotritylation Cross‐Coupling of Aryl Bromides and Iodides to Access Sulfur Functional Groups

Contact Info

Product

Resources

About

Fluoroalkylated hypervalent sulfur fluorides: radical addition of arylchlorotetrafluoro-λ⁶-sulfanes to tetrafluoroethylene