TBAI-catalyzed oxidative cross-coupling of phenols and 2-aminoacetophenones.
TBAI-catalyzed oxidative cross-coupling of phenols and 2-aminoacetophenones.
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DOI：
10.1021/acs.orglett.5b00466
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发表时间：
2015-03
期刊：
影响因子：
5.2
通讯作者：
W. Xu;B. Nachtsheim
中科院分区：
文献类型：
--
作者：
W. Xu;B. Nachtsheim
本文报道了碘催化的苯酚和2-氨基苯乙酮的氧化偶联反应。以四丁基碘化铵（TBAI）为催化剂，叔丁基过氧化氢（TBHP）为助氧化剂，在20 min内合成了一系列α-苯氧基化2-氨基苯乙酮，产率可达92%。这是一个非常罕见的例子碘化物催化的分子间交叉偶联利用酚。然而，这种有效的方法可以进一步扩展到一个分子内的变体，直接获得一系列的二氢-4H-苯并[e][1，3]恶嗪-4-酮。
An iodide-catalyzed oxidative cross-coupling between phenols and 2-aminoacetophenones has been developed. Using catalytic amounts of tetrabutylammoniumiodide (TBAI) as an iodine-containing catalyst and aqueous solutions of tert-butyl hydro-peroxide (TBHP) as the stoichiometric co-oxidant, a variety of α-phenoxylated 2-aminoacetophenones could be obtained in yields of up to 92% after remarkably short reaction times (20 min). This is a very rare example for an iodide-catalyzed intermolecular cross-coupling utilizing phenols. However, this efficient methodology could be further extended toward an intramolecular variant which gives direct access to a range of dihydro-4H-benzo[e][1,3]oxazin-4-ones.