Ligand-Induced Regioselectivity in Metal-Catalyzed Aryne Reactions Using Borylaryl Triflates as Aryne Precursors

Brylon N. Denman, Erin E. Plasek, Courtney C. Roberts

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The utility of reactions using unsymmetrically substituted aryne intermediates can be negatively impacted by issues with regioselectivity as these reactions are substrate controlled. This leaves no avenues for improving regioselectivity without altering the substrate which has led to numerous reports about how to enhance or reverse this regioselectivity in metal-free aryne reactions by changing the electronics. No such studies exist for systems with metal-bound aryne intermediates, which often suffer from worse regioselectivities. Herein we report a means of achieving regioselectivity in a metal-catalyzed aryne difunctionalization via catalyst control. Through the use of an unsymmetrical ligand environment, selectivity can be induced (up to 9:91 r.r.). These investigations demonstrate that catalyst design can influence selectivity in metal-catalyzed aryne reactions.

Original languageEnglish (US)
Pages (from-to)859-864
Number of pages6
JournalOrganometallics
Volume42
Issue number10
DOIs
StatePublished - May 22 2023
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

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