Organocatalysis offers a powerful alternative to metal catalysis because organocatalytic reactions are often less hazardous and more environmentally friendly than metal-catalyzed reactions. We sought to explore the use of quinone organocatalysts to promote the catalytic debenzylation of secondary amines. Therein, a synthetic study towards a substrate and initial debenzylation reactions are described. An appropriate substrate to test the proposed reaction was ultimately synthesized via reductive amination using phenethylamine and benzaldehyde. With this <i>N</i>-benzyl secondary amine in hand, discovery experiments were initiated to test the proposed <i>N</i>-debenzylation by exploring a variety of organoquinone catalysts, bases, and solvents.

Organocatalytic debenzylation of secondary amines

251st National Meeting (2016)

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