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Synthesis of mono- and di-arylated acenaphthylenes and programmed access to dibenzo[: J, l] fluoranthenes via palladium-catalysed C-H bond functionalisation

Abstract : Conditions allowing the C1-arylation and C1,C2-diarylation of acenaphthylenes via palladium-catalysed direct arylation using either aryl bromides or benzenesulfonyl chlorides as aryl sources are reported. With aryl bromides, the mono-arylation was very selective, whereas with benzenesulfonyl chlorides good yields in C1,C2-diarylated acenaphthylenes could be obtained. The reaction tolerates a wide variety of substituents including bromo or iodo. Moreover, the Pd-catalysed intramolecular C-H bond reaction of bromo-substituted C1,C2-diarylated acenaphthylenes provides the corresponding dibenzo[j,l]fluoranthenes. © This journal is the Partner Organisations.
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Submitted on : Friday, March 9, 2018 - 1:48:04 PM
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X. Shi, T. Roisnel, Jean-François Soulé, H. Doucet. Synthesis of mono- and di-arylated acenaphthylenes and programmed access to dibenzo[: J, l] fluoranthenes via palladium-catalysed C-H bond functionalisation. Organic Chemistry Frontiers, Royal Society of Chemistry, 2018, 5 (3), pp.398-408. ⟨10.1039/c7qo00799j⟩. ⟨hal-01713503⟩

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