We are interested in how substrate structure affects the reactivity of tertiary amines in visible light photocatalysis. Hydroxy derivatives of tetrahydroisoquinoline were prepared and oxidatively cyclized to form N,O-acetals. We found that N-aryl and N-alkyl derivatives of this heterocycle are excellent substrates for oxidations using visible light. In contrast, isomeric tetrahydroquinoline substrates were much less reactive and acyclic substrates were unreactive under otherwise identical conditions.

Visible light photooxidation of tertiary amines and anilines

245th National Meeting (2013)

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