Bis(catecholato)germane: an effective catalyst for Friedel-Crafts alkylation reaction
Debayan Basu1, Hari Pada Nayek1
1Department of Chemistry, Indian Institute of Technology (Indian school of Mines), Dhanbad-826004, Jharkhand, India. hpnayek@iitism.ac.in.
Abstract:
Bis(catecholato)germane, [Ge(C6H4O2)2(H2O)2] (1), was synthesized by the reaction of catechol and germanium oxide in water according to a reported method. Complex 1 was characterized by FT-IR spectroscopy, NMR spectroscopy and elemental analysis. Complex 1 was employed as a Lewis acid catalyst in the Friedel-Crafts alkylation reaction of indole with various aldehydes and β-nitrostyrene derivatives separately. The yield of the product for the formation of bis(indolyl)alkanes and nitroalkylated indoles was up to 95% and 96%, respectively. These observations confirmed the catalytic efficacy of complex 1 as a Lewis acid in both reactions. Based on the experimental findings, a plausible mechanism is proposed for both reactions.
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