Convenient and efficient deuteration of functionalized aromatics with deuterium oxide: catalysis by cycloocta-1,5-dienyliridium(I) 1,3-dionates

Aromatic compounds bearing an ortho-directing substituent may be deuterated by exchange with deuterium oxide in the presence of a range of cycloocta-1,5-dienyliridium(1)1,3-dionate catalysts. The exchange takes place in several dipolar aprotic solvents and is directly applicable to the deuteration of polar compounds. Isotope incorporation is efficient and regiospecific. The method is applicable to a wide range of ortho-directing groups some of which are only weak directors for alternative ortho-labelling approaches. In addition, the application of microwaves enables labelling within minutes even with sub-stituents which are poor directors. Copyright (C) 2003 John Wiley Sons, Ltd.