Extension to
 <scp>
 SF
 4
 CF
 3
 </scp>
 and
 <scp>
 SF
 4
 FG
 </scp>
 Groups

Kirsch, Peer

doi:10.1002/9783527824342.ch20

Cited by 7 publications

(2 citation statements)

References 31 publications

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“…Consequently, the resultant SF 4 -containing compounds may exhibit noteworthy deviations in pharmacokinetic attributes, metabolic stability, and binding affinities . Despite its compelling prospects as a bioisosteric entity, the medicinal exploration of SF 4 -incorporating compounds has been constrained due to the dearth of synthetic methodologies for SF 4 -containing molecules. ,, Thus, a pressing demand exists for the development of versatile synthetic toolkits that facilitate the generation of desired hexacoordinated tetrafluorinated sulfur compounds.…”

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confidence: 99%

“…T he trans-tetra-fluorosulfanyl (trans-SF 4 ) group stands as a relatively unexplored fluoro-functional entity, comprising four fluorine atoms and a hypervalent sulfur atom (VI) (Figure 1a). 1 The structural configuration of the SF 4 unit allows for the arrangement of two independent moieties in a linear transconfiguration, rendering SF 4 as a nonconjugated, threedimensional bioisosteric analogue to para-substituted benzene and acetylene derivatives like bicyclo [1.1.1]pentane (BCP) and cubane (Figure 1b). 2 Furthermore, the fluorine atoms within the SF 4 moiety exert substantial influence over lipophilicity and hydrogen bonding interactions.…”

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confidence: 99%

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Cross Dehydrogenative Coupling of SF₄-Alkyne with Tetrahydroisoquinolines

Yadav,

Ariff,

Kawai

et al. 2024

Org. Lett.

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This study introduces a dual-catalytic method for cross-dehydrogenative coupling (CDC) between tetrahydroisoquinolines and Py-SF 4 -alkyne using visible-light photoredox catalysis. This protocol enables selective C(sp 3 )−H alkynylation, expanding the synthetic toolkit for SF 4 -based molecules. Demonstrating efficiency and substrate versatility, this approach opens new avenues in hexacoordinated tetrafluorinated sulfur chemistry and CDC strategies and holds significant promise for drug discovery and materials science.

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confidence: 99%

Cross Dehydrogenative Coupling of SF₄-Alkyne with Tetrahydroisoquinolines

Yadav,

Ariff,

Kawai

et al. 2024

Org. Lett.

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Fluorinated Liquid Crystals

Kirsch

Bremer

2022

Patai's Chemistry of Functional Groups

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The element fluorine is essential for the operation of modern liquid crystal displays (LCDs). It is “visible” to billions of people who mostly are unaware of its presence—in the same room, their pockets, and very often close to their faces. Fluorine makes liquid crystals polar, so they can be switched in an electric field. It imparts conformational rigidity, chemical stability, low polarizability, and viscosity—all crucial factors for the smooth operation of the state‐of‐the‐art LCDs. This chapter presents the syntheses and structure–property relationships of a wide variety of fluorinated materials. Their uses range from standard LCDs to yet unrealized technologies such as Blue Phase displays and future applications of the newly discovered ferroelectric nematic phases. The design of new compounds is often based on rational arguments and a detailed analysis of the physical properties expected for a given structural feature. This is then realized by employing sophisticated synthetic methods unheard of in standard materials chemistry. Even after four decades of research, there is still room for fascination, progress, and surprises.

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Expanding the Frontier of Linear Drug Design: Cu‐Catalyzed C_sp–C_sp³‐Coupling of Electron‐Deficient SF₄‐Alkynes with Alkyl Iodides

Narra,

Bacho,

Hattori

et al. 2023

Advanced Science

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Despite the attractive properties of tetrafluorosulfanyl (SF4) compounds in drug discovery, medicinal research on SF4 molecules is hindered by the scarcity of suitable synthetic methodologies. Drawing inspiration from the well‐established Sonogashira cross‐coupling of terminal alkynes under Pd‐catalysis, it is envisioned that SF4‐alkynes can serve as effective coupling partners. To overcome the challenges associated with the electron‐deficient nature of SF4‐alkynes and the lability of the SF4 unit under transition‐metal catalysis, an aryl radical mediated Csp–Csp3 cross‐coupling reaction is successfully developed under Cu catalysis. This methodology facilitates the coupling of SF4‐alkynes with alkyl iodides, leading to the immediate synthesis of SF4‐attached drug‐like molecules. These findings highlight the potential impact of SF4‐containing molecules in the drug industry, paving the way for further research in this emerging field.

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Extension to SF ₄ CF ₃ and SF ₄ FG Groups

Cited by 7 publications

References 31 publications

Cross Dehydrogenative Coupling of SF₄-Alkyne with Tetrahydroisoquinolines

Cross Dehydrogenative Coupling of SF₄-Alkyne with Tetrahydroisoquinolines

Fluorinated Liquid Crystals

Expanding the Frontier of Linear Drug Design: Cu‐Catalyzed C_sp–C_sp³‐Coupling of Electron‐Deficient SF₄‐Alkynes with Alkyl Iodides

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Extension to SF 4 CF 3 and SF 4 FG Groups

Cited by 7 publications

References 31 publications

Cross Dehydrogenative Coupling of SF4-Alkyne with Tetrahydroisoquinolines

Cross Dehydrogenative Coupling of SF4-Alkyne with Tetrahydroisoquinolines

Fluorinated Liquid Crystals

Expanding the Frontier of Linear Drug Design: Cu‐Catalyzed Csp–Csp3‐Coupling of Electron‐Deficient SF4‐Alkynes with Alkyl Iodides

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Product

Resources

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Extension to SF ₄ CF ₃ and SF ₄ FG Groups

Cross Dehydrogenative Coupling of SF₄-Alkyne with Tetrahydroisoquinolines

Cross Dehydrogenative Coupling of SF₄-Alkyne with Tetrahydroisoquinolines

Expanding the Frontier of Linear Drug Design: Cu‐Catalyzed C_sp–C_sp³‐Coupling of Electron‐Deficient SF₄‐Alkynes with Alkyl Iodides