Synthesis of Pyridine-SF4-Alkynes via Light-Promoted Radical Coupling of Pyridine-SF4-Chlorides and EBX Reagents

Mahmoud, Elsayed M.; Iwasaki, Hiroto; Hada, Kenshiro; Murata, Yusuke; Sumii, Yuji; Shibata, Norio

doi:10.1246/bcsj.20220330

Cited by 8 publications

(1 citation statement)

References 47 publications

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“…Several radical addition reactions of ArSF 4 Cl compounds have been reported thus far (Scheme 1A, right). 5 c ,10 These synthetic methods are considerably milder than conventional direct fluorination of sulfides and have enabled the preparation of a variety of aromatic compounds with the tetrafluoro-λ 6 -sulfanyl (SF 4 ) moiety. However, radical addition reactions of ArSF 4 Cl compounds to fluoroolefins have not been reported.…”

Section: Introductionmentioning

confidence: 99%

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

Yasuo,

Aikawa,

Nozaki

et al. 2023

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

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

Yasuo,

Aikawa,

Nozaki

et al. 2023

Chem. Sci.

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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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Regio‐ and Z‐Selective Alkyne Hydroamination and Hydrophenoxylation using Tetrafluoro‐λ⁶‐Sulfanyl Alkynes under Superbasic, Naked Anion Conditions

et al. 2023

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Alkyne hydroamination is an effective approach for the production of enamines and enaminecontaining N-heterocycles. However, stereoselectivity control is a considerable challenge in this reaction because of the electronic repulsion between an incoming nitrogen lone pair and the alkyne π-system. Herein, we propose a methodology involving β-regio-and Zselective alkyne hydroamination by using tetrafluoro-λ 6sulfanyl (SF 4 ) alkynes under superbasic, naked anion conditions. The reaction is compatible with a wide variety of N-heterocycles, including indoles, carbazoles, pyrazoles, and imidazoles, and selectively furnishes SF 4linked Z-vinyl enamines with β-regioselectively. Moreover, the method can be extended to the β-and Zcontrolled, base-mediated alkyne hydrophenoxylation with phenols to provide SF 4 -linked Z-vinyl ethers in high yields. As the SF 4 unit has attracted attention as a bioisostere for alkynes, p-benzenes, bicyclo[1.1.1]pentyl (BCP) groups, and cubanes in medicinal chemistry, this chemistry represents an effective approach to creating novel drug candidates incorporating SF 4 -containing molecules.

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Synthesis of Pyridine-SF4-Alkynes via Light-Promoted Radical Coupling of Pyridine-SF4-Chlorides and EBX Reagents

Cited by 8 publications

References 47 publications

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

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

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

Regio‐ and Z‐Selective Alkyne Hydroamination and Hydrophenoxylation using Tetrafluoro‐λ⁶‐Sulfanyl Alkynes under Superbasic, Naked Anion Conditions

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Synthesis of Pyridine-SF4-Alkynes via Light-Promoted Radical Coupling of Pyridine-SF4-Chlorides and EBX Reagents

Cited by 8 publications

References 47 publications

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

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

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

Regio‐ and Z‐Selective Alkyne Hydroamination and Hydrophenoxylation using Tetrafluoro‐λ6‐Sulfanyl Alkynes under Superbasic, Naked Anion Conditions

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

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

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

Regio‐ and Z‐Selective Alkyne Hydroamination and Hydrophenoxylation using Tetrafluoro‐λ⁶‐Sulfanyl Alkynes under Superbasic, Naked Anion Conditions