Recyclable chiral dinuclear copper(II) complexes catalyzed asymmetric Friedel–Crafts alkylation of 1-naphthol using N-tosyl aldimine

Kumari, Prathibha; Jakhar, Ajay; Khan, Noor‐ul H.; Tak, Rajkumar; Kureshy, Rukhsana I.; Abdi, Sayed H. R.; Bajaj, Hari C.

doi:10.1016/j.catcom.2015.06.002

Cited by 20 publications

(7 citation statements)

References 28 publications

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“…To explore the general applicability of the catalysts in the addition reaction of aryl and alkyl aldimines with naphthols these were screened. Among these, the active binuclear Cu(II)‐ 8 catalyst was found to be most efficient and the products were obtained in good to excellent yield with high ee ’s (Scheme ) . The recovered catalyst worked well for the asymmetric addition reaction between 1‐naphthol and aldimine (R=Ph) without any apparent loss in its reactivity and enantioselectivity up to six cycles.…”

Section: Chiral Catalystsmentioning

confidence: 99%

Direct Asymmetric Arylation of Imines

et al. 2020

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The Friedel-Crafts reaction represents one of the most efficient tools for the formation of carbon-carbon bonds and direct derivatization of aromatic compounds. Asymmetric arylation of imines involving Friedel-Crafts reaction has received much interest recently. The present review summarizes the works on the asymmetric arylation of imines by different approaches including Friedel-Crafts reaction and their development to date. The review is divided into three main sections: addition reaction of arenes to imines in the presence of chiral catalysts; addition reaction of arenes to imines containing chiral tails and asymmetric coupling reaction of aryl boronic acids and imines. 4.2. Palladium Catalysts with Chiral Ligands 4.3. Nickel Catalysts with Chiral Ligands 5. Conclusions

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Section: Chiral Catalystsmentioning

confidence: 99%

Direct Asymmetric Arylation of Imines

et al. 2020

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“…The catalyst can be recovered and reused at least six times without losing efficiency. 24 Finally, in 2014, Feng reported the reaction of sesamol and aromatic aldimines catalyzed by a Sc(III) complex with a chiral N,N′-dioxide ligand 6 (Scheme 18). 25 This method delivered the corresponding reaction products with enantiomeric excesses higher than those obtained using Chimni's procedure.…”

Section: Scheme 17 Reactions Of 2-naphthols With N-tosyl Aldimines Camentioning

confidence: 99%

Catalytic Enantioselective Friedel–Crafts Reactions of Naphthols and Electron-Rich Phenols

et al. 2016

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The enantioselective Friedel-Crafts reaction is a powerful tool for the construction of benzylic stereocenters in a stereodefined manner. Significant advances have already been achieved with heteroarenes such as indoles and pyrroles; however, the reaction with homoarenes is less developed. This short review covers the most relevant literature on enantioselective Friedel-Crafts reactions with naphthols and phenols. 1 Introduction 2 Friedel-Crafts Reactions Involving 1,2-Nucleophilic Addition to C=X Bonds 3 Friedel-Crafts Reactions Involving Conjugate Nucleophilic Addition to Electrophilic C=C Bonds 4 Friedel-Crafts Reactions Involving π-Allylic Complexes as Electrophiles 5 ipso-Friedel-Crafts Reactions 6 Conclusions

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“…Chiral complexes have important applications in many fields such as enantioselective catalysts, material sciences, metallo-supramolecular chemistry and bio-inorganic modeling studies [1]. They catalyze various asymmetric organic transformations giving high enantioselectivity [2,3]. In recent years, Schiff-bases derived from chiral amino alcohols and their transition metal complexes have been reported to catalyze the enantioselective Henry reaction [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

et al. 2019

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Abstract. Three new copper(II) complexes (1-3) with general formula [Cu(HL)CH3COO] of N-salicyl-β-amino alcohol Schiff bases containing, (S)-(+)-phenyl glycinol, (1S, 2R)-2-amino-1, 2-diphenylethanol and 1, 1, 3-triphenyl-(R)-(+)-2-amino propanol, were synthesized. Their structures were characterized by FTIR, LCMS, magnetic moment, molar conductance and elemental analysis data. DFT calculations proposed distorted square planar geometries for the complexes. The calculated IR spectra are in good agreement with the experimental IR spectra, confirming the proposed structures. Their interactions with calf thymus DNA were investigated and their binding constants Kb were found. Gel electrophoresis reveals that all complexes display significant nuclease activity against supercoiled pentry/d-topo plasmid DNA. Resumen. Tres nuevos complejos de cobre (II) (1-3) con la fórmula general [Cu (HL) CH3COO] de N-salicil-β-amino alcohol Schiff bases que contienen, (S) - (+) - fenilglicinol, (1S, 2R). Se sintetizaron -2-amino-1, 2-difeniletanol y 1, 1, 3-trifenil- (R) - (+) - 2-amino propanol. Sus estructuras se caracterizaron por FTIR, LCMS, momento magnético, conductancia molar y datos de análisis elemental. Los cálculos de DFT propusieron geometrías planas cuadradas distorsionadas para los complejos. Los espectros de IR calculados están en buena concordancia con los espectros de IR experimentales, confirmando las estructuras propuestas. Se investigaron sus interacciones con el ADN del timo de ternera y se encontraron sus constantes de unión Kb. La electroforesis en gel revela que todos los complejos muestran una actividad nucleasa significativa contra el ADN plasmídico pentry / d-topo superenrollado.

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Recyclable chiral dinuclear copper(II) complexes catalyzed asymmetric Friedel–Crafts alkylation of 1-naphthol using N-tosyl aldimine

Cited by 20 publications

References 28 publications

Direct Asymmetric Arylation of Imines

Direct Asymmetric Arylation of Imines

Catalytic Enantioselective Friedel–Crafts Reactions of Naphthols and Electron-Rich Phenols

DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

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