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

TETRAHEDRON

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Article

Marquise, Nada¹  Harford, Philip J.²  Chevallier, Floris¹  Roisnel, Thierry³  Dorcet, Vincent³  Gagez, Anne-Laure⁵  Sable, Sophie⁵  Picot, Laurent⁵  Thiery, Valerie⁵  Wheatley, Andrew E. H.²  Gros, Philippe C.⁴  Mongin, Florence¹ 

[1] Univ Rennes 1, Inst Sci Chim Rennes, UMR 6226, CNRS, F-35042 Rennes, France

[2] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[3] Univ Rennes 1, Ctr Diffractometrie X, Inst Sci Chim Rennes, CNRS,UMR 6226, F-35042 Rennes, France

[4] Univ Lorraine, CNRS, HECRIN, SRSMC, F-54506 Vandoeuvre Les Nancy, France

[5] Univ La Rochelle, LIENSs UMR 7266, F-17042 La Rochelle, France

关键词: Deprotometalation;    Copper;    Lithium;    Heterocycle;    Palladium;   

DOI  :  10.1016/j.tet.2013.09.030

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

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