Journal
ORGANIC LETTERS
Volume 21, Issue 7, Pages 2256-2260Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00532
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- Ministry of Science and Technology ROC [MOST 107-2113-M-003-003]
- National Taiwan Normal University [103-07-C]
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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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