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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

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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.

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

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Publication details

The article was received on 05 Sep 2017, accepted on 04 Oct 2017 and first published on 11 Oct 2017


Article type: Research Article
DOI: 10.1039/C7QO00799J
Citation: Org. Chem. Front., 2018, Advance Article
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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

    X. Shi, T. Roisnel, J. Soulé and H. Doucet, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00799J

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