Rapid, Microwave-Assisted Perdeuteration of Polycyclic Aromatic Hydrocarbons

A simple and convenient method for the perdeuteration of polycyclic aromatic hydrocarbons that does not require strong acid has been developed. Using commercially available reagents, the one-step procedure provides a new route to perdeuterated derivatives of both common and exotic polycyclic aromatic hydrocarbons. Microwave irradiation of the hydrocarbons in a solution of dimethylformamide-d(7) containing potassium tert-butoxide affords rapid and essentially complete H/D exchange. For example, corannulene is converted to corannulene-d(10) with >98% deuterium incorporation in just 1 h of microwave irradiation in a solution of t-BuOK/DMF-d(7).