Synthesis of bis- and tris(indolyl)methanes catalyzed by an inorganic nano-sized catalyst followed by dehydrogenation to hyperconjugated products

• Published in: Journal of the Serbian Chemical Society Vol. 81; no. 9; pp. 1069 - 1079
• Main Authors: Khorshidi Alireza, Shariati Shahab, Abootalebi Masoomeh
• Format: Journal Article
• Language: English
• Published: Serbian Chemical Society 01-01-2016
• Subjects: (indolyl)methane; dehydrogenation; KIT-6; magnetite; Solid acid
• ISSN: 0352-5139; 1820-7421
• DOI: 10.2298/JSC160207052K

A set of bis- and tris(indolyl)methanes were prepared and dehydrogenated to their hyperconjugated products in a one-pot fashion. Nano-sized-SO3H functionalized mesoporous KIT-6 coated on magnetite nanoparticles (Fe3O4@SiO2@KIT-6-OSO3H) was used as an efficient catalyst in the first step of synthesis, and dehydrogenation was performed by using (NH4)2S2O8 after removal of the catalyst. The catalyst was fully characterized by Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM) and X-ray powder diffraction (XRD), as well as nitrogen adsorption-desorption isotherms. The bis- and tris(indolyl)methanes were studied by UV-Vis spectroscopy before and after dehydrogenation, and effect of the ambient parameters on their spectra was investigated. It was found that bis- and tris(indolyl)methanes have no considerable absorption in the visible range and what makes them colorful is partial dehydrogenation due to exposure to air. Our catalyst as a new combination of known materials, showed superiority in terms of yield, time, and mild reaction conditions in comparison with previous reports.