Design and application of a novel and effective ligand for the Cu-catalyzed amination of aryl halides in water

Wang, Lifang; Zhu, Xinhai; Liang, Zexuan; Huang, Manna; Wan, Yiqian

doi:10.1080/17518253.2022.2147027

Green Chemistry Letters and Reviews

2022

DOI: 10.1080/17518253.2022.2147027

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Design and application of a novel and effective ligand for the Cu-catalyzed amination of aryl halides in water

Lifang Wang

Xinhai Zhu

Zexuan Liang

et al.

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Cited by 3 publications

References 36 publications

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Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe₃O₄@SiO₂ Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction

Pourshahi,

Mansoori,

Ghahramani

et al. 2024

ChemistrySelect

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The present work describes the grafting of a polymer‐metal chelate (PMC) from Fe3O4@SiO2 core‐shells via the Surface Initiated‐Atom Transfer Radical Polymerization (SI‐ATRP). The magnetic core‐shells were silylated by 2‐bromo‐2‐methyl‐N‐(3‐(trimethoxysilyl)propanamide (BTPAm) to give the surface‐anchored ATRP initiator. Acrylamide was polymerized from the Fe3O4@SiO2 surface via the ATRP approach. The grafted magnetic nanoparticles were trans‐amidated with ethylenediamine to give poly(N‐2‐aminoethylacrylamide) grafted magnetic core‐shells, Fe3O4@SiO2‐g‐PAE‐AAm. The grafted chelating polymer ligand (CPL) was treated with an acetonitrile solution of CuI to afford the Fe3O4@SiO2‐g‐PAE‐AAm−Cu(I). The grafted PMC was characterized by FT‐IR, CP/MAS 13C NMR, and thermo‐gravimetric analysis (TGA). The grafted PMC catalyzed the N−C bond formation via the Ullmann‐type N‐arylation reaction of haloarenes and anilines under optimal reaction conditions. Mono N‐arylation product was obtained as the major product with excellent selectivity. The excellent recyclability of the catalyst was shown by negligible deactivation over six runs.

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Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe₃O₄@SiO₂ Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction

Pourshahi,

Mansoori,

Ghahramani

et al. 2024

ChemistrySelect

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Room-Temperature CuI-Catalyzed N-Arylation of Cyclopropylamine

Hong,

Zhu,

Lai

et al. 2023

J. Org. Chem.

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A general and efficient CuI/N-carbazolyl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the N-arylation of cyclopropylamine using aryl bromides at room temperature. Herein, 5 mol % CuI and 5 mol % of the ligand were used to synthesize N-aryl cyclopropylamines in moderate to excellent yields. This protocol was scaled up to produce the desired product at gram levels and has been generalized for C−N coupling between aryl bromides and amines at room temperature.

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Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water

Hong,

Wang,

Zhu

et al. 2024

Org. Lett.

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A novel protocol for the Cu-catalyzed reductive N-arylation of nitroarenes with (hetero)aryl chlorides in water has been realized. Combining N-(9H-carbazol-9-yl)-6-hydroxypicolinamide (L2) with oxalohydrazide is vital to realize the method at 90 °C with a loading of 5 mol % of Cu 2 O/L2. Various nitroarenes and aryl chlorides have been successfully coupled in good to excellent isolated yields. Further, two diarylamine-containing key intermediates, 3f and 4u, have been smoothly synthesized on a gram scale using this method.

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Design and application of a novel and effective ligand for the Cu-catalyzed amination of aryl halides in water

Cited by 3 publications

References 36 publications

Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe₃O₄@SiO₂ Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction

Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe₃O₄@SiO₂ Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction

Room-Temperature CuI-Catalyzed N-Arylation of Cyclopropylamine

Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water

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Design and application of a novel and effective ligand for the Cu-catalyzed amination of aryl halides in water

Cited by 3 publications

References 36 publications

Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe3O4@SiO2 Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction

Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe3O4@SiO2 Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction

Room-Temperature CuI-Catalyzed N-Arylation of Cyclopropylamine

Copper-Catalyzed One-Pot Protocol for Reductive N-Arylation of Nitroarenes with (Hetero)aryl Chlorides in Water

Contact Info

Product

Resources

About

Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe₃O₄@SiO₂ Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction

Poly(N‐2‐Aminoethylacrylamide)‐Cu(I) Chelate Grafted from Fe₃O₄@SiO₂ Core‐Shells for the Selective Monoarylation of Anilines via the Ullmann Reaction