Peri-Xanthenoxanthene (PXX): A Versatile Organic Photocatalyst in Organic Synthesis
April 2021
in “
Advanced synthesis & catalysis
”
peri-Xanthenoxanthene PXX organic photocatalyst photocatalyst radical reactions carbon-carbon bonds carbon-heteroatom bonds dual catalytic systems nickel-catalyzed cross-coupling reactions ß-arylation cyclic ketones photophysical studies EPR studies electrochemical data photoreducing catalyst iridium complexes photoredox reactions
TLDR PXX is an effective and affordable photocatalyst for creating new chemical bonds in organic synthesis.
The document from April 2021 reports on the effectiveness of peri-Xanthenoxanthene (PXX) as a versatile and cost-effective organic photocatalyst in organic synthesis. PXX's highly reducing excited state allows for the activation of various substrates, leading to radical reactions and the formation of new carbon-carbon and carbon-heteroatom bonds. The study showcases PXX's use in benchmark transformations, dual catalytic systems, and the synthesis of an important intermediate for the investigational drug setipiprant. It also details PXX's role in nickel-catalyzed cross-coupling reactions and the ß-arylation of cyclic ketones, with reaction yields ranging from less than 5% to 82%. Mechanistic insights are provided through photophysical, EPR studies, and electrochemical data, confirming PXX's function as a photoreducing catalyst. The findings emphasize PXX's potential as a low-cost alternative to more expensive photocatalysts like iridium complexes, with broad applicability in photoredox reactions.
