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Synlett 2024; 35(07): 747-752
DOI: 10.1055/s-0042-1751487
DOI: 10.1055/s-0042-1751487
synpacts
Insights into the Regioselectivity of Metal-Catalyzed Aryne Reactions
The University of Minnesota is acknowledged for startup funds. We also acknowledge the National Institutes of Health (NIH) (R35GM146957) for funds. Instrumentation for the UMN Chemistry NMR facility was supported from a grant through the NIH (S10OD011952). E.E.P. was funded by the Newman and Lillian Bortnick fellowship and B.N.D was funded by the Robert and Jill DeMaster fellowship.
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.
1 Introduction
2 Inducing Regioselectivity via Ligand Control
3 A Comparison of o-Borylaryl Triflate Aryne Precursors to Kobayashi Aryne Precursors
4 Conclusion
Publication History
Received: 01 July 2023
Accepted after revision: 31 July 2023
Article published online:
18 September 2023
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