Benzimidazole-Based Carboxyl Functionalized Porphyrin with Enhanced Photocatalytic Activity Towards Metal Free Sonogashira Coupling

Raut, Subodh Uttamrao; Balinge, Kamlesh Rudreshwar; Bhansali, Karan Jeevanlal; Deshmukh, Shubham; Bhagat, Pundlik Rambhau

doi:10.1007/s10562-022-04154-5

Cited by 8 publications

(1 citation statement)

References 59 publications

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“…Furthermore, the elimination of the acetylenic hydrogen atom (TMS) forms the desired aryl acetylenes. In parallel work, in 2022, Bhagat and co-workers 48 demonstrated a visible-light-driven methodology for Sonogashira coupling reaction with a metal-free carboxyl functionalised benzimidazolium ionic liquid-based porphyrin photocatalyst (MFCFBILPc) (Scheme 20). The synthesis of MFCFBILPc was achieved in five steps beginning with 2-hydroxybenzaldehyde.…”

Section: Metal-free Organo-photocatalysis Sonogashira Reactionsmentioning

confidence: 99%

Photochemical Sonogashira coupling reactions: beyond traditional palladium–copper catalysis

Singh,

Shaikh

2023

Chem. Commun.

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Section: Metal-free Organo-photocatalysis Sonogashira Reactionsmentioning

confidence: 99%

Photochemical Sonogashira coupling reactions: beyond traditional palladium–copper catalysis

Singh,

Shaikh

2023

Chem. Commun.

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Reducible Drug Pyrazinamide as a Powerful Ligand to Assist Copper (II)‐Catalyzed N‐Arylation

Chai,

Wang,

2024

Applied Organom Chemis

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Herein, pyrazinamide (L1) was used as a powerful ligand to promote a CuSO4‐catalyzed reaction between aryl halides and imidazole (HID) under mild conditions, generating various N‐arylation products in good to excellent yields. The findings indicate that CuSO4 was reduced and coordinated with L1 to form [CuIL1], which activated ArX to produce [ArCuIL1X] through oxidative addition. This intermediate subsequently underwent reductive elimination to form N‐arylation products, with [ArCuILID] being generated from a reaction between [ArCuIL1X] and HID. This method was successfully extended to the synthesis of 2‐phenylindole and pyrrolo[1,2‐a]quinoxaline under mild conditions. The method significantly enhances the efficiency and cost effectiveness of C‐N coupling reaction.

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Recent Applications of the Sonogashira Reaction in the Synthesis of Drugs and Their Derivatives: A Review

Yan,

Zhang,

et al. 2024

Applied Organom Chemis

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Metal‐catalyzed cross‐coupling reactions are essential tools for constructing C–C bonds in organic synthesis. Among these prominent approaches, the Sonogashira reaction stands out as a key player and is widely utilized in medicinal chemistry. This versatile method enables the creation of complex C (sp2)–C (sp) bonds by linking aryl or vinyl halides with terminal alkynes, facilitating the efficient construction of molecular structures crucial for drug development. A notable application of the Sonogashira reaction is its ability to incorporate aromatic and alkynyl functionalities into pharmaceutical compounds. Depending on the impactful catalytic system evolved gradually, the Sonogashira reaction can involve either double‐metal catalysis or single‐metal catalysis. This review sheds light on the diverse applications of the Sonogashira coupling approach in drug synthesis and the generation of their derivatives.

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Benzimidazole-Based Carboxyl Functionalized Porphyrin with Enhanced Photocatalytic Activity Towards Metal Free Sonogashira Coupling

Cited by 8 publications

References 59 publications

Photochemical Sonogashira coupling reactions: beyond traditional palladium–copper catalysis

Photochemical Sonogashira coupling reactions: beyond traditional palladium–copper catalysis

Reducible Drug Pyrazinamide as a Powerful Ligand to Assist Copper (II)‐Catalyzed N‐Arylation

Recent Applications of the Sonogashira Reaction in the Synthesis of Drugs and Their Derivatives: A Review

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