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

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

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...

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Veröffentlicht in:Organic letters 2019-04, Vol.21 (7), p.2256-2260
Hauptverfasser: Ichake, Sachin S, Villuri, Bharath Kumar, Reddy, Sabbasani Rajasekhara, Kavala, Veerababurao, Yao, Ching-Fa
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container_end_page 2260
container_issue 7
container_start_page 2256
container_title Organic letters
container_volume 21
creator Ichake, Sachin S
Villuri, Bharath Kumar
Reddy, Sabbasani Rajasekhara
Kavala, Veerababurao
Yao, Ching-Fa
description 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.
doi_str_mv 10.1021/acs.orglett.9b00532
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title A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C–H Bond Alkenylation
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