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金催化芳氧基炔的高效合成 2,4-二取代呋喃。

Gold-catalyzed efficient synthesis of 2,4-disubstituted furans from aryloxy-enynes.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, People's Republic of China.

出版信息

Org Biomol Chem. 2012 Apr 21;10(15):2960-5. doi: 10.1039/c2ob07173h. Epub 2012 Mar 9.

Abstract

A series of (E)-1-aryloxy-1-en-3-ynes has been prepared by Sonogashira coupling of 2-bromo-3-aryloxypropenoates with terminal alkynes using Pd(PPh(3))(4) and CuI as the catalysts in Et(3)N. The resulting enynyl-aryl ethers are found to be highly applicable to the synthesis of 2,4-disubstituted furans with an ester group at C-4 position through an Au/Ag-catalyzed annulation reaction under extremely mild reaction conditions.

摘要

通过使用 Pd(PPh(3))(4)和 CuI 作为催化剂,在 Et(3)N 中对 2-溴-3-芳氧基丙烯酸盐与末端炔烃进行 Sonogashira 偶联反应,制备了一系列(E)-1-芳氧基-1-烯-3-炔。发现所得的烯基芳基醚非常适用于通过 Au/Ag 催化的环化反应在极其温和的反应条件下合成在 C-4 位具有酯基的 2,4-二取代呋喃。

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