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Org Lett. 2016 Jul 15;18(14):3342-5. doi: 10.1021/acs.orglett.6b01438. Epub 2016 Jul 5.

Efficient Route to Deuterated Aromatics by the Deamination of Anilines.

Author information

1
Institute of Molecular and Translation Medicine, Faculty of Medicine, Palacký University , Hněvotínská 5, 779 00 Olomouc, Czech Republic.
2
Department of Organic Chemistry, Faculty of Science, Palacký University , 771 46 Olomouc, Czech Republic.

Abstract

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.

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