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Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions

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A catalytic method for the synthesis of substituted fluoranthenes that operates via tandem Suzuki–Miyaura and intramolecular C–H arylation reactions is reported. The overall reaction sequence works effectively with homogeneous catalysis… Click to show full abstract

A catalytic method for the synthesis of substituted fluoranthenes that operates via tandem Suzuki–Miyaura and intramolecular C–H arylation reactions is reported. The overall reaction sequence works effectively with homogeneous catalysis using Pd(dppf)Cl2 as well as heterogeneous catalysis using reduced graphene oxide (rGO)-CuPd nanocatalysts with low catalyst loadings. High functional group tolerance is observed under both catalytic conditions where arylboronic acids and esters having electron-withdrawing and electron-donating substituents afforded fluoranthene products in good yields (up to 78%). Moreover, the rGO-CuPd nanocatalysts are demonstrated to be reusable by preserving almost 90% of their initial activity after the third cycle.

Keywords: intramolecular arylation; via tandem; tandem suzuki; suzuki miyaura; miyaura intramolecular; arylation reactions

Journal Title: ACS Omega
Year Published: 2017

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