Hauser鈥揌eck: Efficient Synthesis of 纬-Aryl-尾-ketoesters en Route to Substituted Naphthalenes

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• 作者：Frederic Wagner ; Klaus Harms ; Ulrich Koert
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 20, 2015
• 年：2015
• 卷：17
• 期：22
• 页码：5670-5673
• 全文大小：352K
• ISSN：1523-7052

文摘

纬-Aryl-尾-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)₂/t-Bu₃P and stoichiometric amounts of Bu₃SnF. The wide range of 纬-(hetero)aryl-尾-ketoesters that can be obtained illustrate the scope and limitations of this novel Hauser鈥揌eck combination. 纬-Aryl-尾-ketoesters with a 1,3-dioxane acetal in the ortho position can easily be transformed into the hydroxy naphthoate in very good yield. Aqueous formic acid at 65 掳C provides optimal conditions for this deprotective aromatization.