Photoredox-Catalyzed Radical-Radical Coupling of Potassium Trifluoroborates with Acyl Azoliums

Michael J. Rourke, Matthew J. McGill, Daniel Yang, Emelia J. Farnam, Joshua L. Zhu, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Potassium trifluoroborates have gained significant utility as coupling partners in organic synthesis, particularly in the Suzuki Miyaura coupling reaction. Recently, they have also been used as radical precursors under oxidative conditions to generate carbon-centered radicals. These versatile reagents have found new applications in photoredox catalysis, including radical substitution, conjugate-addition reactions, and transition-metal dual catalysis. In addition, this photomediated redox-neutral process has enabled radical radical coupling with persistent radicals in the absence of a metal, and this process remains to be fully explored. In this study, we report the radical radical coupling of potassium benzylic trifluoroborate salts with isolated acyl azolium triflates, which are persistent-radical precursors. The reaction is catalyzed by an organic photocatalyst and forms isolable tertiary alcohol species. These products can be transformed into a range of substituted ketone products by simple treatment with a mild base.

Original languageEnglish (US)
Pages (from-to)2175-2180
Number of pages6
JournalSynlett
Volume34
Issue number18
DOIs
StatePublished - May 4 2023

Funding

The authors thank Northwestern University for support of this work. We also thank Charlotte Stern (NU) for X-ray crystallographic analysis.

Keywords

  • acyl azolium compounds
  • ketones
  • organophotocatalysis
  • photoredox catalysis
  • potassium trifluoroborate
  • radical-radical coupling

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Photoredox-Catalyzed Radical-Radical Coupling of Potassium Trifluoroborates with Acyl Azoliums'. Together they form a unique fingerprint.

Cite this