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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 acenaphthylene 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.

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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., 2017, Accepted Manuscript
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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. Soule and H. Doucet, Org. Chem. Front., 2017, Accepted Manuscript , DOI: 10.1039/C7QO00799J

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