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†
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.