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

Nada Marquise; Philip Harford; Floris Chevallier; Thierry Roisnel; Vincent Dorcet; Anne-Laure Gagez; Sophie Sablé; Laurent Picot; Valérie Thiéry; Andrew Wheatley; Philippe Gros; Florence Mongin

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

Nada Marquise ¹ Philip Harford ² Floris Chevallier ¹ Thierry Roisnel ¹ Vincent Dorcet ¹ Anne-Laure Gagez ³ Sophie Sablé ³ Laurent Picot ³ Valérie Thiéry ^{3, *} Andrew Wheatley ^{2, *} Philippe Gros ⁴ Florence Mongin ¹

* Corresponding author

1 ISCR - Institut des Sciences Chimiques de Rennes

2 Department of Chemistry

3 LIENSs - LIttoral ENvironnement et Sociétés - UMR 7266

4 SRSMC - Structure et Réactivité des Systèmes Moléculaires Complexes

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.

keyword : Deprotometalation Copper Lithium Heterocycle Palladium

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Journal articles

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Chemical Sciences / Other

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

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

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