1. An ionic liquid mediated Friedel-Crafts addition of arenes to isothiocyanates
- Author
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Naik, Prashant U., Nara, Susheel J., Harjani, Jitendra R., and Salunkhe, Manikrao M.
- Subjects
Solvents -- Composition ,Catalysts -- Composition ,Thiols ,Amides ,Ionic solutions ,Chemical compounds -- Composition ,Chemical research -- Analysis - Abstract
A new protocol is developed for the synthesis of N-substituted thioamides, employing arenes and isothiocyanates in 1-butyl-3-methylimidazolium chloroaluminate ionic liquid, [bmim]Cl*2Al[Cl.sup.3], as a homogenous Lewis acid catalyst and solvent. The effect of Lewis acidity and the stoichiometry of the ionic liquid on the extent of product formation is studied. Studies reveal that a progressive increase in yields was observed with increasing Lewis acidity, and two equivalents of [bmim]Cl*2Al[Cl.sup.3] was the optimal amount for the reaction. A distinct para selectivity for the incoming thioamido group on activated arenes was observed under ambient conditions. Key words: arenes, isothiocyanates, Friedel-Crafts, ionic liquids, thioamides.
- Published
- 2003