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Aerobic and Electrochemical Oxidative Cross‐Dehydrogenative‐Coupling (CDC) Reaction in an Imidazolium‐Based Ionic Liquid |
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| Authors: | Olivier Baslé Dr. Nadine Borduas Pauline Dubois Jean Marc Chapuzet Dr. Tak‐Hang Chan Prof. Jean Lessard Prof. Chao‐Jun Li Prof. |
| Affiliation: | 1. Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, QC H3A 2K6 (Canada), Fax: (+1)‐514‐398‐3797;2. Department of Chemistry, Sherbrooke University, 2500 boul. de l'Université Sherbrooke, Sherbrooke QC J1K 2R1 (Canada), Fax: (+1)‐819‐821‐8017 |
| Abstract: | The ionic liquid 1‐butyl‐3‐methylimidazolium tetrafluoroborate [BMIm][BF4] has demonstrated high efficiency when applied as a solvent in the oxidative nitro‐Mannich carbon? carbon bond formation. The copper‐catalyzed cross‐dehydrogenative coupling (CDC) between N‐phenyltetrahydroisoquinoline and nitromethane in [BMIm][BF4] occurred with high yield under the described reaction conditions. Both the ionic liquid and copper catalyst were recycled nine times with almost no lost of activity. The electrochemical behavior of the tertiary amine substrate and β‐nitroamine product was investigated employing [BMIm][BF4] as electrolyte solvent. The potentiostatic electrolysis in ionic liquid afforded the desired product with a high yield. This result and the cyclic voltammetric investigation provide a better understanding of the reaction mechanism, which involves radical and iminium cation intermediates. |
| Keywords: | cations C?C coupling C?H activation ionic liquids oxidation |