Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation

Abstract : The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6-tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents.
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Nada Marquise, Philip Harford, Floris Chevallier, Thierry Roisnel, Vincent Dorcet, et al.. Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation. Tetrahedron, Elsevier, 2013, 69 (47), pp.10123-10133. ⟨10.1016/j.tet.2013.09.030⟩. ⟨hal-00869376⟩

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