Trioctylmethylphosphonium nitrate (P8,8,8,1NO3), an ionic liquid made via a green synthesis, catalyses electrophilic aromatic chlorination of arenes with HCl and air at 80 °C. The aromatic oxychlorination is truly catalytic in nitrate, proceeds without added solvents, and uses atmospheric oxygen as oxidant. The extent of chlorination can be controlled to yield selectively mono or 10 dichlorinated products, and the ionic liquid catalyst can be recycled. Dependence of the rate on HCl and nitrate concentrations as well as on the rate of re-oxidation of the nitrogen intermediates by air, allowed to propose a chlorination mechanism.
Phosphonium nitrate ionic liquid catalysed electrophilic aromatic oxychlorination
NOE', Marco;PEROSA, Alvise;SELVA, Maurizio;
2010-01-01
Abstract
Trioctylmethylphosphonium nitrate (P8,8,8,1NO3), an ionic liquid made via a green synthesis, catalyses electrophilic aromatic chlorination of arenes with HCl and air at 80 °C. The aromatic oxychlorination is truly catalytic in nitrate, proceeds without added solvents, and uses atmospheric oxygen as oxidant. The extent of chlorination can be controlled to yield selectively mono or 10 dichlorinated products, and the ionic liquid catalyst can be recycled. Dependence of the rate on HCl and nitrate concentrations as well as on the rate of re-oxidation of the nitrogen intermediates by air, allowed to propose a chlorination mechanism.
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