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Issue 39, 2014
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Copper-catalyzed direct alkylation of 1,3-azoles with N-tosylhydrazones bearing a ferrocenyl group: a novel method for the synthesis of ferrocenyl-based ligands

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Abstract

Copper-catalyzed cross-coupling of ferrocenyl ketone-derived N-tosylhydrazones with benzo[d]oxazole leads to the direct C–H bond functionalization by a secondary ferrocenyl alkyl group. This direct C–H bond alkylation of azoles with N-tosylhydrazones bearing a ferrocenyl group uses inexpensive CuBr as the catalyst without any ligand. The reaction is operationally simple and conducted under mild conditions, giving the corresponding ferrocenyl-based ligands in moderate to good yields. Furthermore, they were able to act as bidentate ligands, giving rise to the corresponding palladium chelated complex 6a–6c, which were obtained by reaction of 5a–5c with [PdCl2(MeCN)2].

Graphical abstract: Copper-catalyzed direct alkylation of 1,3-azoles with N-tosylhydrazones bearing a ferrocenyl group: a novel method for the synthesis of ferrocenyl-based ligands

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Supplementary files

Article information


Submitted
28 May 2014
Accepted
28 Jul 2014
First published
29 Jul 2014

Org. Biomol. Chem., 2014,12, 7721-7727
Article type
Paper

Copper-catalyzed direct alkylation of 1,3-azoles with N-tosylhydrazones bearing a ferrocenyl group: a novel method for the synthesis of ferrocenyl-based ligands

Q. Teng, J. Hu, L. Ling, R. Sun, J. Dong, S. Chen and H. Zhang, Org. Biomol. Chem., 2014, 12, 7721
DOI: 10.1039/C4OB01093K

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