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Updated: Jun 8, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Insights into the Regioselectivity of Metal-Catalyzed Aryne Reactions
Erin E Plasek1, Brylon N Denman1, Courtney C Roberts1
1University of Minnesota, Department of Chemistry, 225 Pleasant Street SE, Minneapolis, MN 55455, USA.
Abstract:
The synthetic potential of unsymmetrically substituted aryne intermediates is significantly hindered by regioselectivity issues. Current methods for inducing regioselectivity all rely on substrate control and are focused on non-metallated arynes. Before our initial disclosure, there was no systematic study regarding the regioselectivity of metal-catalyzed aryne reactions. By exploiting ligand control, we have induced regioselectivity in a palladium-catalyzed aryne annulation to form phenanthridinones (up to 9:91 r.r.). Through this study we have investigated: ligand effects, influence of steric perturbation, and the impact of the aryne precursor.
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