An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl₄

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• 作者：Gourhari Maiti ; ^{ghmaiti123@yahoo.co.in} ; Utpal Kayal ; Rajiv Karmakar ; Rudraksha N. Bhattacharya
• 关键词：2H-Chromenes ; Dihydrochalcones ; Hydration-rearrangement sequence ; HAuCl4
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：21 November, 2012
• 年：2012
• 卷：53
• 期：47
• 页码：6321-6325
• 全文大小：3676 K

文摘

2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl₄ are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group.