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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.
Cited literature [7 references]
https://hal.archives-ouvertes.fr/hal-00869376
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Wednesday, October 16, 2013 - 9:44:55 AM
Last modification on : Wednesday, May 18, 2022 - 11:20:03 AM
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Wednesday, October 16, 2013 - 9:44:55 AM
Last modification on : Wednesday, May 18, 2022 - 11:20:03 AM
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