Functionalized imidazolium salt: an efficient catalyst for Buchwald–Hartwig type C–N cross-coupling of (hetero)aryl chlorides/bromides with amines under solvent-, inert gas-, and base-free ambience

Jana, Barun; Gautam, Deepak; Gahlaut, Puneet Singh; Yadav, Kapil

doi:10.1039/d2nj04254a

Cited by 6 publications

(1 citation statement)

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“…11,12 Similarly, several carbon-based polydentate ligands (carbenes) are used to achieve high reactivity in metathesis reactions. 13,14 Based on the above-described knowledge, the use of the 1,2,3-triazolepyridine ligand as bidentate chelating ligands also increased proportionally due to its easy accessibility via a Cu(I) catalyzed ''click'' reaction where under ambient conditions terminal alkyne and azide combined in very high yields [Scheme 1]. 15 1,2,3-Triazoles are significant because of their applications in catalysis, 16,17 separation, 18 biomedical applications, e.g.…”

Section: Introductionmentioning

confidence: 99%

Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd(ii) complex: application in the Suzuki–Miyaura coupling reaction

et al. 2023

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Section: Introductionmentioning

confidence: 99%

Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd(ii) complex: application in the Suzuki–Miyaura coupling reaction

et al. 2023

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A chemoselective and one‐pot method for the synthesis of unsymmetrical secondary amines via coupling reaction of ammonia and aryl(alkyl) halides catalyzed by MNP@IAH@Cu‐IL as a bifunctional nanocatalyst

Nosratollahi,

Soleiman‐Beigi,

Norouzi

2024

Applied Organom Chemis

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Copper, an abundant metal on Earth, has re‐emerged as a suitable alternative to versatile Palladium‐catalyzed C–N coupling. Herein, a new recoverable and reusable bifunctional catalyst was synthesized by combining an ionic liquid and linking Cu(II) on the surface of Fe3O4 nanoparticles. New nanocatalyst (MNP@IAH@Cu‐IL) was completely characterized using different techniques. Continuing, MNP@IAH@Cu‐IL was applied in the synthesis of primary and secondary amines via C(sp2)‐N coupling reaction successfully. This catalyst worked well in the synthesis of anilines derivatives in high yields and excellent quality. Further, we described a novel and one‐pot process for the synthesis of unsymmetrical secondary amine derivatives from two different aryl(alkyl) halides. This procedure shows attractive features such as 100% atom economy, high yields of the desired products under base‐free conditions, excellent functional group tolerance, work‐up simplicity, and recyclability.

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H₂O ⋅ B(C₆F₅)₃‐Catalyzed para‐Alkylation of Anilines with Alkenes Applied to Late‐Stage Functionalization of Non‐Steroidal Anti‐Inflammatory Drugs

Winfrey,

Yun,

Passeri

et al. 2024

Chemistry A European J

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Anilines are core motifs in a variety of important molecules including medicines, materials and agrochemicals. We report a straightforward procedure that allows access to new chemical space of anilines via their para‐C−H alkylation. The method utilizes commercially available catalytic H2O ⋅ B(C6F5)3 and is highly selective for para‐C‐alkylation (over N‐alkylation and ortho‐C‐alkylation) of anilines, with a wide scope in both the aniline substrates and alkene coupling partners. Readily available alkenes are used, and include new classes of alkene for the first time. The mild reaction conditions have allowed the procedure to be applied to the late‐stage‐functionalization of non‐steroidal anti‐inflammatory drugs (NSAIDs), including fenamic acids and diclofenac. The formed novel NSAID derivatives display improved anti‐inflammatory properties over the parent NSAID structure.

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Functionalized imidazolium salt: an efficient catalyst for Buchwald–Hartwig type C–N cross-coupling of (hetero)aryl chlorides/bromides with amines under solvent-, inert gas-, and base-free ambience

Abstract: The intermingle of novel imidazolium salt (HL1 -Br) and Cu(OAc)2 marked down as a highly efficient catalytic system for Buchwald-Hartwig type C-N Coupling of a variety of amines with (hetero)...

Cited by 6 publications

References 38 publications

Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd(ii) complex: application in the Suzuki–Miyaura coupling reaction

Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd(ii) complex: application in the Suzuki–Miyaura coupling reaction

A chemoselective and one‐pot method for the synthesis of unsymmetrical secondary amines via coupling reaction of ammonia and aryl(alkyl) halides catalyzed by MNP@IAH@Cu‐IL as a bifunctional nanocatalyst

H₂O ⋅ B(C₆F₅)₃‐Catalyzed para‐Alkylation of Anilines with Alkenes Applied to Late‐Stage Functionalization of Non‐Steroidal Anti‐Inflammatory Drugs

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Functionalized imidazolium salt: an efficient catalyst for Buchwald–Hartwig type C–N cross-coupling of (hetero)aryl chlorides/bromides with amines under solvent-, inert gas-, and base-free ambience

Abstract: The intermingle of novel imidazolium salt (HL1 -Br) and Cu(OAc)2 marked down as a highly efficient catalytic system for Buchwald-Hartwig type C-N Coupling of a variety of amines with (hetero)...

Cited by 6 publications

References 38 publications

Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd(ii) complex: application in the Suzuki–Miyaura coupling reaction

Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd(ii) complex: application in the Suzuki–Miyaura coupling reaction

A chemoselective and one‐pot method for the synthesis of unsymmetrical secondary amines via coupling reaction of ammonia and aryl(alkyl) halides catalyzed by MNP@IAH@Cu‐IL as a bifunctional nanocatalyst

H2O ⋅ B(C6F5)3‐Catalyzed para‐Alkylation of Anilines with Alkenes Applied to Late‐Stage Functionalization of Non‐Steroidal Anti‐Inflammatory Drugs

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H₂O ⋅ B(C₆F₅)₃‐Catalyzed para‐Alkylation of Anilines with Alkenes Applied to Late‐Stage Functionalization of Non‐Steroidal Anti‐Inflammatory Drugs