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

Autor: Rourke, Michael J., McGill, Matthew J., Yang, Daniel, Farnam, Emelia J., Zhu, Joshua L., Scheidt, Karl A.
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Zdroj: Synlett; Nov2023, Vol. 34 Issue 18, p2175-2180, 6p
Abstrakt: Keywords: potassium trifluoroborate; photoredox catalysis; organophotocatalysis; acyl azolium compounds; radical-radical coupling; ketones EN potassium trifluoroborate photoredox catalysis organophotocatalysis acyl azolium compounds radical-radical coupling ketones 2175 2180 6 10/31/23 20231127 NES 231127 Graph Organoboron compounds have long been recognized for providing chemists with unique strategies for carbon-carbon bond formation. [41] Shortly after, we reported the applications of isolated acyl azoliums and expanded our methods to include both stoichiometric ester azoliums and three-component radical-relay reactions, which employed potassium trifluoroborates as radical precursors in the photoredox-mediated alkoxycarbonylation of trifluoroborates and synthesis of -aryloxy ketones. [33] However, under appropriate conditions radical-radical coupling is favored when (a) radicals are generated at equivalent rates, such as in photoredox-mediated reactions, and (b) the radicals exhibit different lifetimes, with one radical being persistent and the other transient. Potassium trifluoroborate, photoredox catalysis, acyl azolium compounds, radical-radical coupling, organophotocatalysis, ketones. [Extracted from the article]
Databáze: Complementary Index