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A PEG/copper(I) halide cluster as an eco-friendly catalytic system for C–N bond formation

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Abstract

The catalytic activities of eight copper(I) halide clusters assembled from copper(I) halide and ferrocenyltelluroethers, 1–8, were investigated in C–N formation under various conditions. A catalytic procedure using poly(ethylene glycol) (PEG-400) as a greener alternative organic solvent has been developed. The PEG-400/5 system can achieve 99% targeted yield with a mild reaction temperature and short reaction time. After the isolation of the products by extraction with diethyl ether, this PEG-400/cluster system could be easily recycled. Spectroscopic studies elucidate a stepwise mechanism: firstly, proton-coupled electron transfer (PCET) involving the transfer of an electron from Cu+ and a proton from imidazole results in the formation of a labile penta-coordinated Cu2+ and aryl radical; the following effective electron transfer from the ferrocene unit reduces Cu2+ and forms the target product; finally, the ferrocenium unit is reduced by the I anion. The merits of this eco-friendly synthesis are the efficient utilization of reagents and easy recyclability.

Graphical abstract: A PEG/copper(i) halide cluster as an eco-friendly catalytic system for C–N bond formation

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Publication details

The article was received on 04 Apr 2018, accepted on 28 Apr 2018 and first published on 30 Apr 2018


Article type: Paper
DOI: 10.1039/C8DT01310A
Citation: Dalton Trans., 2018, Advance Article
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    A PEG/copper(I) halide cluster as an eco-friendly catalytic system for C–N bond formation

    C. Li, W. Ji, J. Qu, S. Jing, F. Gao and D. Zhu, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C8DT01310A

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