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Synthesis 2018; 50(19): 3911-3920
DOI: 10.1055/s-0037-1609578
DOI: 10.1055/s-0037-1609578
paper
An Effective Heterogeneous Copper Catalyst System for C–N Coupling and Its Application in the Preparation of 2-Methyl-4-methoxydiphenylamine (MMDPA)
This work was supported by grants from the National Natural Science Foundation of China (21702239), Guangzhou Science and Technology Plan Projects (201707010271), the Fundamental Research Funds for the Central Universities (16lgpy16), and the Funds of Sun Yat-sen University (2017sdjgpy010).
Further Information
Publication History
Received: 07 May 2018
Accepted after revision: 13 June 2018
Publication Date:
25 July 2018 (online)
Abstract
A ligand-recyclable, environmentally benign heterogeneous catalyst system composed of CuI and polystyrene-supported N(-(4-(aminomethyl)naphthalen-1-yl)-N(-phenyl-1H-pyrrole-2-carbohydrazide (PSAP) has been established for Ullmann type C–N coupling based on the homogeneous catalyst system N′,N′-diphenyl-1H-pyrrole-2-carbohydrazide/CuI. This heterogeneous catalyst system maintained the catalytic effectiveness of the homogeneous catalyst. A variety of functionalized aryl bromides can be efficiently aminated with aryl amines and aliphatic amines with high selectivity for amines over alcohols. Moreover, a practical application of this catalyst system to promote the reaction of commercially available 4-methoxy-2-methylaniline and bromobenzene in 10 mmol scale, provided 2-methyl-4-methoxydiphenylamine (MMDPA) with 93% yield with the merit of the approach being simple operation for work-up and purification.
Key words
heterogeneous catalysis - copper catalysis - C–N coupling - recyclability - 2-methyl-4-methoxydiphenylamine (MMDPA)Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609578.
- Supporting Information
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