Thioxanthone-photocatalyzed aerobic oxidation of N,N-dimethylanilines to N-formyl anilines under visible light
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. piotr.szczesniak@icho.edu.pl.
Abstract:
A mild and efficient photo-induced method for the direct oxidation of N,N-dimethylanilines using inexpensive, commercially available thioxanthone as a photocatalyst is reported. The reaction proceeds under ambient conditions, in the presence of oxygen and visible light. The resulting formamides can be directly converted into N-methylalanines via a one-pot deformylation process, offering a practical and sustainable strategy for the demethylation of N,N-dimethylanilines. The methodology is operationally simple, scalable, and compatible with structurally diverse substrates. Its synthetic utility was further demonstrated through late-stage functionalization of value added molecules, including Padimate O, Thioflavin T, Mifepristone and Tropinone.
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