A ruthenium-based catalytic system for nucleophilic aromatic substitution (SNAr) is investigated through the synthesis and full characterization of proposed intermediates. Using the reaction of morpholine and flurorobenzene as a model reaction, SNAr is shown to proceed quickly at room temperature while subsequent arene exchange is shown to require elevated temperature. Further, arene binding is shown to have a thermodynamic preference for product arene binding over fluoroarene binding by a factor of 2,000. Analysis of the catalyst resting state suggests that cyclometallation of the phosphine ligand is not vital for catalytic activity.

Nucleophilic aromatic substitution catalyzed by η6-ruthenium complexes: Lessons in catalyst design and product inhibition

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.