Highly Efficient and Reusable Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides

A Young Kim,Hyunjoon Song,Hyun Ju Lee,Haesik Yang,Hyunju Kang,Kang Hyun Park,Ji Chan Park

doi:10.3390/molecules14125169

A Young Kim, Hyunjoon Song + Show 5 more

Open Access

https://doi.org/10.3390/molecules14125169

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Abstract

CuO/AB was found to be a simple and efficient catalyst for the N-arylation of a variety of nitrogen-containing heterocycles, giving the products in excellent yields.

Highlights

IntroductionThe copper-mediated C-heteroatom (C-N, C-O, C-S, C-P, C-Se), C-C, and C-metal bonds formations are pivotal transformations that have been developed to include a wide range of substrates
The copper-mediated C-heteroatom (C-N, C-O, C-S, C-P, C-Se), C-C, and C-metal bonds formations are pivotal transformations that have been developed to include a wide range of substrates.the N-arylation of nitrogen-containing heterocycles is of particular interest as the resulting products represent important structural motifs of numerous natural products and biologically active compounds
Despite the significant progress made in the development of copper catalyzed coupling reactions of this type, there still exists a need for new methods that involve cheap andenvironmentally sound catalysts [7–9]

Summary

Introduction

The copper-mediated C-heteroatom (C-N, C-O, C-S, C-P, C-Se), C-C, and C-metal bonds formations are pivotal transformations that have been developed to include a wide range of substrates. Classical Ullmann chemistry, along with closely related methods, have been known for a full century. This copper-mediated synthesis of biaryl is known as the Molecules 2009, 14. During the first 70 years of the 20th century, copper was nearly the only metal usable for aryl-aryl bond formation, finding initial in the reductive symmetrical coupling of aryl halides, corresponding aromatic compounds, aryl halides, diaryl ether, N-containing reactants, phenols, and related nucleophilic agents [10–18]. Mild and highly efficient CuI-catalyzed N-arylation procedures for nitrogencontaining heterocycles (imidazoles, benzimidazoles, pyrroles, pyrazoles, indoles, triazoles) with aryl and heteroaryl halides have been developed [19–22]. The CuO hollow nanospheres were used to catalyze the N-arylation of nitrogen-containing heterocycles with aryl halides

Results and Discussion

Catalyst characterization

Reaction test

General remarks

Synthesis of CuO hollow nanospheres

Conclusions