Abstract
A safe and efficient method for catalytic H/D exchange to provide high deuterium incorporation into a variety of aromatic substrates was developed. Systematic screening of the catalyst and activator revealed that the essential activation of the Pd or Rh catalyst could be achieved under safe and user friendly conditions. The application of this simple catalytic method for the deuteration of bi- and tricyclic aromatic compounds and chiral natural products was investigated.
Key words
deuterium - palladium - rhodium - heterogenous catalysis - alkaloids
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Typical Reaction Conditions.
Into a sealed tube under argon was given 1.00 mmol organic compound, 10 weight% catalyst, 5 mol% NaBD4 (98% D) and 3 mL D2O (99% D). The mixture was stirred for approximately 30 s and the tube was sealed (remark: the reaction vessel was closed not until bubbling had stopped) and heated to 130 °C for 18 h. The mixture was cooled to r.t. and 3 mL MeCN were added. The catalyst was separated by filtration. The product was purified by chromatography if necessary and analyzed by NMR and LC-MS.
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