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.