Application of 1-butyl-3-methylimidazolium hexafluorophosphate to Ir(I)-catalyzed hydrogen isotope exchange labelling of substrates poorly soluble in dichloromethane
✍ Scribed by Rhys Salter; Isabelle Bosser
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- French
- Weight
- 107 KB
- Volume
- 46
- Category
- Article
- ISSN
- 0022-2135
- DOI
- 10.1002/jlcr.692
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✦ Synopsis
Abstract
Substrate solubility remains a major limitation in Ir(I)‐catalyzed isotopic hydrogen exchange labelling. In the search for an alternative to the solvent dichloromethane, which is critical to the success of the reaction, we examined a series of ionic liquids for their suitability. Commercially available 1‐butyl‐3‐methylimidazolium hexafluorophosphate (abbreviated to [BMI][PF~6~]) was found to support efficient deuterium and tritium exchange labelling of N‐(4‐methoxyphenyl)‐N‐methyl benzamide 1 under standard conditions. The solvent dissolves both polar hydroxyl and carboxylic acid substituted acetanilides, providing isotopomers in unprecedentedly high deuterium incorporation as compared to dichloromethane. We report the application of [BMI][PF~6~] and its potential for extending the scope of Ir(I)‐catalyzed H/T exchange to more polar compounds. Copyright © 2003 John Wiley & Sons, Ltd.