Over the past 14 years, the Wolfe group has developed a series of Pd-catalyzed coupling reactions between alkenes bearing pendant nucleophiles and carbon-centered electrophiles, such as aryl halides, that afford substituted heterocycles. We have recently developed a new variant of these alkene difunctionalization reactions that utilize nitrogen-centered electrophiles, derived from acylated hydroxylamines. The coupling of these electrophiles with N-allylguanidines and ureas afford heterocyclic alkene diamination products. This presentation will describe our studies on the scope of this reaction, along with efforts to improve the stereospecific generation of products that result from either anti or syn addition to the alkene. Preliminary mechanistic findings will also be presented, including studies to determine whether these transformations proceed through a Pd(0)/(II) vs Pd(II)/(IV) catalytic cycle.

New developments in palladium-catalyzed alkene diamination reactions of nitrogen electrophiles

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.