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A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation

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Abstract

The palladium catalyzed synthesis of 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives as core polycyclic aromatic hydrocarbons (PAHs) was achieved via an intramolecular annulation and decyanogenative C-H bond alkenylation strategy. A readily synthesized Knoevenagel condensation product of [1,1′-biphenyl]-2,2′-dicarbaldehyde with benzyl cyanide converted successfully into 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives in excellent yields up to 94%. The transformation involves an intramolecular cascade C-C bond formation along with a C-H bond cleavage sequence.

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Ichake, S. S., Villuri, B. K., Reddy, S. R., Kavala, V., & Yao, C. F. (2019). A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation. Organic Letters, 21(7), 2256–2260. https://doi.org/10.1021/acs.orglett.9b00532

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