Allylamines are synthetically valuable and ubiquitous in various biologically active classes of compounds. The C–H activation of amines is very challenging because of complications with the coordination of the amine, including beta–hydride elimination and substrate decomposition in the presence of transition metal catalysts. Various approaches have been developed to functionalize the gamma position of primary amines using stoichiometric directing groups and specific ligands that do not offer step economy. Although transient directing groups have been developed to improve step economy, they only work with primary, and not secondary, amine substrates. Meanwhile, there are many challenges with performing C–H activation on allyl groups, including their increased sensitivity to hydrofunctionalization or difunctionalization (especially in the presence of Pd catalysts), as well as the regio and site–selectivity issues because of various accessible C–H bonds. This study describes carbon dioxide in the form of dry ice, as a transient directing group to selectively functionalize gamma C–H bonds of primary and secondary allylamines using a palladium catalyst.

Palladium–catalyzed gamma–arylation of allylamines using dry ice

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.