Memoirs of the Graduate Schools of Engineering and System Informatics Kobe University, No. 2, pp. 8-11, 2010

An Unexpected Reaction in the Copper/silver-catalyzed Oxidative Dimerization of Imidazole Derivatives

Takashi SOMETE1, Daiki MONGUCHI1, Yuji MIYAZAKI1, Atsunori MORI1

1Graduate School of Engineering, Department of Chemical Science and Engineering

(Received November 4, 2010; Accepted December 14, 2010; Online published December 17, 2010)

Keywords: Oxidative dimerization, N-Methyl-benzimidazole, Copper catalyst, Mass spectrum, CH functionalization

An unexpected side reaction takes place in the oxidative dimerization of an imidazole derivative catalyzed by CuCl2 (10 mol%) and Ag2CO3 (20 mol%). Unidentified product, whose estimated molecular weight is 278, is obtained along with the dimerized product at the CH bond at the 2-position (MW = 262). Measurements of NMR and mass spectra and several transformation reactions suggest a possible structure.

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