Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation
Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation
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DOI：
10.1016/j.tet.2013.09.030
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发表时间：
2013-11-25
期刊：
影响因子：
2.1
通讯作者：
Mongin, Florence
中科院分区：
文献类型：
--
作者：
Marquise, Nada;Harford, Philip J.;Mongin, Florence
研究了由CuX（X=Cl，Br）和LiTMP（TMP= 2，2，6，6-四甲基哌啶并，2当量）合成的锂铜酸盐对2-氯吡啶脱铜-芳酰化反应的影响。CuCl被确定为比CuBr更适合用于此目的的铜源。以这种方式从吖嗪和噻吩合成了在芳基之一的2位上带有卤素的不同的二芳基酮。然后，这些参与钯催化的闭环：底物进行预期的CH-活化型芳基化，得到芴酮型化合物，并进行环化反应，导致氧杂蒽酮，特别是在含氧取代基或试剂的存在下。(C)2013作者由爱思唯尔有限公司出版。保留所有权利。
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.