Efficient Route to Deuterated Aromatics by the Deamination of Anilines

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

¹⁹F spectra of 9a at different temperatures.

<p>¹⁹F spectra of 9a at different temperatures.</p

Copper-free click reaction with dibenzoazocine 7 and azides 5 and 6.

<p>Copper-free click reaction with dibenzoazocine 7 and azides 5 and 6.</p

Two conformers 1 and 2 of derivative 8a with different positions of the aliphatic chain.

<p>Two conformers 1 and 2 of derivative 8a with different positions of the aliphatic chain.</p

Cyclooctynes for copper-free click reactions.

<p>Cyclooctynes for copper-free click reactions.</p

Numbering of atoms in 8a,b and 9a,b in the conformational study.

<p>Numbering of atoms in 8a,b and 9a,b in the conformational study.</p

Preparation of triazoles 10, 11 and 12.

<p>Preparation of triazoles 10, 11 and 12.</p

¹H NMR spectra of 9a at different temperatures.

<p>¹H NMR spectra of 9a at different temperatures.</p

The most abundant conformation of derivative 8b.

<p>The most abundant conformation of derivative 8b.</p

Preparation of azides 5 and 6.

<p>Preparation of azides 5 and 6.</p