A palladium-catalyzed Catellani-type [2+2+2] annulation reaction of aryl iodides, bromothiophenes, and norbornadiene, which proceeds via a tandem Heck coupling/double C-H bond activation and retro-Diels-Alder pathway to access thiophene-fused polyaromatics, is reported. The key feature of this protocol represents a NBD/NBE retaining annulation.
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Palladium-Catalyzed Modular Synthesis of Thiophene-Fused Polycyclic Aromatics via Sequential C-H Activation.
Org Lett
January 2025
Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China.
A palladium-catalyzed Catellani-type [2+2+2] annulation reaction of aryl iodides, bromothiophenes, and norbornadiene, which proceeds via a tandem Heck coupling/double C-H bond activation and retro-Diels-Alder pathway to access thiophene-fused polyaromatics, is reported. The key feature of this protocol represents a NBD/NBE retaining annulation.
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We have shown that palladium-catalyzed cascade processes provide modular access to rigid quinoline-containing tetracyclic amines. This modular approach enables fine-tuning of the through-space charge transfer (TSCT) state formation between the lone pair localized on the nitrogen atom in the cage moiety and the quinoline moiety by variation of both the intramolecular -aryl distance and quinoline substitution. Decreasing this -aryl distance enhances the formation of the TSCT species, giving control over the emission color and photoluminescence quantum yield.
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