SBA-15 Immobilized Phenanthroline–Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N–H Heterocycles with Aryl Halides

Hosseinzadeh, Rahman; Aghili, Nora; Tajbakhsh, Mahmood

doi:10.1007/s10562-015-1622-4

Cited by 23 publications

(10 citation statements)

References 55 publications

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“…Although many ligands have been found to promote the catalytic Goldberg reaction, diamine ligands appeared to be good candidates for the proposed study. Based on the work of Buchwald [ 14 , 15 , 16 ], Hosseinzadeh [ 17 , 18 , 19 ], and Ribas [ 20 ], 1,10-phenanthroline (phen) was chosen as the ligand for this project as it is inexpensive and has occasionally been found to be effective for some Goldberg reactions at low catalyst loading with a Cu/ligand ratio of 1/1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction

Comins

2022

Molecules

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A short and economical synthesis of various 2-methylaminopyidine amides (MAPA) from 2-bromopyridine has been developed using the catalytic Goldberg reaction. The effective catalyst was formed in situ by the reaction of CuI and 1,10-phenanthroline in a 1/1 ratio with a final loading of 0.5–3 mol%. The process affords high yields and can accommodate multigram-scale reactions. A modification of this method provides a new preparation of 2-N-substituted aminopyridines from various secondary N-alkyl(aryl)formamides and 2-bromopyridine. The intermediate aminopyridine formamide is cleaved in situ through methanolysis or hydrolysis to give 2-alkyl(aryl)aminopyridines in high yields.

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Section: Introductionmentioning

confidence: 99%

Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction

Comins

2022

Molecules

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“…As another example of a heterogenized homogeneous catalyst, Hosseinzadeh and co‐workers published an interesting study on the application of a phenantroline‐Cu I complex immobilized on SBA‐15 for the N ‐arylation of amides and N−H heterocycles. This Cu I ‐complex catalyst allowed the use of both aryl iodides and bromides, but required the use of an excess of the corresponding aryl halide (2 : 1 molar ratio) [12c] . Very recently, copper(0) nanoparticles supported on charcoal were reported as efficient catalyst for the N ‐arylation of primary benzamides and lactams with aryl iodides.…”

Section: Introductionmentioning

confidence: 99%

Copper Nanoparticles Supported on Zinc Oxide as Efficient Catalyst for the N‐Arylation of (Hetero)cyclic and Acyclic Amides

et al. 2021

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Copper nanoparticles (CuNPs) supported on ZnO are highly active and selective heterogeneous catalyst for the N-arylation of cyclic and acyclic amides (Golberg coupling). The reaction conditions are mild, featuring K 3 PO 4 as a base and N,N'dimethylethylendiamine (DMEDA) as ligand in refluxing acetonitrile. The CuNPs/ZnO catalyst can be recovered and reused in six cycles with only little loss of activity. The methodology can be successfully scaled up to gram scale without decreasing the catalytic activity.

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“…[32] Although there are various reports in the literature about the use of copper complexes immobilized on mesoporous silica materials as catalysts in the N-arylation reaction, in most of them, the reactions were carried out in toxic organic solvents and at high temperatures. [14,[33][34][35] So, there is a strong requirement to develop new and more efficient recoverable catalytic systems for the N-arylation reaction that can be operated under mild reaction condition in an environmentally friendly reaction media. Herein, we reported the immobilization of a copper Schiff base complex on the surface of amino-modified MCM-41, aiming at developing a new green catalyst.…”

Section: Introductionmentioning

confidence: 99%

Preparation, Characterization and Application of Copper Schiff base Complex Supported on MCM‐41 as a Recyclable Catalyst for the Ullmann‐type N‐arylation Reaction

2020

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In this study, a Cu‐Schiff base complex supported on highly ordered mesoporous silica MCM‐41 was successfully prepared to form a heterogeneous catalyst. The structural and textural properties of the newly prepared catalyst were determined by various microscopic and spectroscopic techniques such as FT‐IR, BET, TGA, DRS UV‐vis, EDX, XPS, ICP‐OES, XRD, and TEM. The catalyst was used in the N‐arylation of various amines through formation of intramolecular C(aryl)‐N bond from the relevant aryl halides (Ar−I and Ar−Br) with amines by coupling reactions of Ullmann type. The significant advantages of this protocol were generality, low metal content, high yield of products, and simple work‐up procedure. Moreover, the catalyst could be recycled efficiently for seven runs without any appreciable decrease in reactivity and no leaching of copper was found during this course.

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SBA-15 Immobilized Phenanthroline–Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N–H Heterocycles with Aryl Halides

Cited by 23 publications

References 55 publications

Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction

Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction

Copper Nanoparticles Supported on Zinc Oxide as Efficient Catalyst for the N‐Arylation of (Hetero)cyclic and Acyclic Amides

Preparation, Characterization and Application of Copper Schiff base Complex Supported on MCM‐41 as a Recyclable Catalyst for the Ullmann‐type N‐arylation Reaction

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