期刊
TETRAHEDRON
卷 69, 期 47, 页码 10123-10133出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.09.030
关键词
Deprotometalation; Copper; Lithium; Heterocycle; Palladium
资金
- Agence Nationale de la Recherche (ACTIVATE program)
- CPER Poitou-Charentes
- Comite 17 de la Ligue contre le Cancer
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. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
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