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Issue 15, 2018
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N-Arylation of ferrocenyl 2,4-thiazolidinedione conjugates via a copper-catalysed Chan–Lam cross coupling reaction with aryl boronic acids and their optoelectronic properties

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Abstract

A copper catalyzed Chan–Lam type N-arylation protocol has been applied to achieve moderate to good yields of N-arylated ferrocenyl 2,4 thiazolidinedione conjugates. A general and mild strategy has been developed for the cross-coupling of aryl boronic acids and ferrocenyl 2,4 thiazolidinedione conjugates. This coupling was achieved through the use of copper(II) acetate and screened for different bases, solvents and a variety of arylboronic acids including electron-withdrawing and electron-donating groups. All the new compounds were obtained as red crystalline solids. The solid state structure of (3b) was established by single crystal X-ray diffraction analysis. All the compounds were fully characterized by 1H and 13C NMR, FT-IR, ESI-mass, UV-Visible and fluorescence spectroscopies. Electrochemical studies (CV) showed reversible one-electron oxidation and the conjugates were found to be stable in organic solvents. Furthermore, these ferrocenyl 2,4-thiazolidinedione conjugates (3b, 3f, 3i, 3k, and 3l) exhibited good to moderate antidiabetic activities.

Graphical abstract: N-Arylation of ferrocenyl 2,4-thiazolidinedione conjugates via a copper-catalysed Chan–Lam cross coupling reaction with aryl boronic acids and their optoelectronic properties

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Publication details

The article was received on 02 Apr 2018, accepted on 08 Jun 2018 and first published on 11 Jun 2018


Article type: Paper
DOI: 10.1039/C8NJ01598H
Citation: New J. Chem., 2018,42, 12587-12594
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    N-Arylation of ferrocenyl 2,4-thiazolidinedione conjugates via a copper-catalysed Chan–Lam cross coupling reaction with aryl boronic acids and their optoelectronic properties

    D. N. Shinde, R. Trivedi, J. V. S. Krishna, L. Giribabu, B. Sridhar, P. S. Khursade and R. S. Prakasham, New J. Chem., 2018, 42, 12587
    DOI: 10.1039/C8NJ01598H

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