Amine oxidation is a potent tool for the production of a broad range of synthetic intermediates, such as imines, amides, oximes, nitro compounds, nitriles, aldehydes, and ketones. The conventional route to aldehydes and ketones involves the oxidation of primary and secondary alcohols, alternatively, the synthesis of carbonyl compounds could be achieved from readily available and abundant precursors like amines. Herein, we report an efficient protocol for oxidation of benzyl amines to corresponding aldehyde or ketone. Our new method involves use of commercially available (diethylamino)sulfur trifluoride (DAST) as reagent combined with DMSO as solvent and oxidant. The reaction provided carbonyl compounds in excellent yields with high purity and short reaction times. All the reactions were carried out a in a screw-cap glass vial at ambient temperature without maintaining moisture-free or inert conditions. In all cases, formation of the corresponding carbonyl compounds was observed exclusively without any traces of carboxylic acid as further oxidation product.

Oxidative deamination of benzyl amines to carbonyl compounds promoted by (Diethylamino)sulfur trifluoride (DAST)

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.