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

X. Shi (1) , T. Roisnel (1) , Jean-François Soulé (1) , H. Doucet (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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.

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

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, 2018, 5 (3), pp.398-408. ⟨10.1039/c7qo00799j⟩. ⟨hal-01713503⟩