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氧化芳族碳-氧键的形成:通过氯化铁介导的α-芳基酮闭环反应合成3-官能化苯并[b]呋喃

Oxidative aromatic C-O bond formation: synthesis of 3-functionalized benzo[b]furans by FeCl3-mediated ring closure of alpha-aryl ketones.

作者信息

Liang Zhidan, Hou Weizhe, Du Yunfei, Zhang Yongliang, Pan Yan, Mao Deng, Zhao Kang

机构信息

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.

出版信息

Org Lett. 2009 Nov 5;11(21):4978-81. doi: 10.1021/ol902157c.

Abstract

A variety of 3-functionalized benzo[b]furans were achieved by way of a FeCl(3)-mediated intramolecular cyclization of electron-rich alpha-aryl ketones. The alkoxy substituent on the benzene ring in the substrates was essential for an efficient cyclization to occur. This novel method allows the construction of benzo[b]furan rings by joining the O-atom on the side chain to the benzene ring via direct oxidative aromatic C-O bond formation.

摘要

通过富电子α-芳基酮的FeCl₃介导分子内环化反应,实现了多种3-官能化苯并[b]呋喃的合成。底物苯环上的烷氧基取代基对于高效环化反应的发生至关重要。这种新方法通过直接氧化形成芳族C-O键,将侧链上的O原子与苯环相连,从而构建苯并[b]呋喃环。

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