Efficient Route to Deuterated Aromatics by the Deamination of Anilines

Article abstract of DOI:10.1021/acs.orglett.6b01438

One-step replacement of NH₂ groups in ring-substituted anilines by deuterium is reported. Approaches comprising both solid-phase and solution-phase syntheses can be used on a large variety of substrates. The method uses diazotization in a mixture of water and either dichloromethane or chloroform, which serve as a source of hydrogen. This protocol can be used as a general method for fast and easy incorporation of deuterium into an aromatic system using deuterated chloroform.