Substituted alkyne synthesis under nonbasic conditions: copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling.
Substituted alkyne synthesis under nonbasic conditions: copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling.
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DOI：
10.1021/ol006807d
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发表时间：
2001-01
期刊：
影响因子：
5.2
通讯作者：
C. Savarin;J. Šrogl;L. S. Liebeskind
中科院分区：
文献类型：
--
作者：
C. Savarin;J. Šrogl;L. S. Liebeskind
[图：见正文]描述了一种合成取代炔的新方法。在噻吩-2-羧酸铜（I）（CuTC）或3-甲基水杨酸铜（I）（CuMeSal）的存在下，钯催化的硫代炔衍生物与硼酸的交叉偶联以39%至91%的产率提供官能化炔。这种偶联在温和的非碱性条件下有效地与各种各样的硫代炔和硼酸发生，提供了与Sonogashira协议互补的反应。
[figure: see text] A new methodology for the synthesis of substituted alkynes is described. In the presence of copper(I) thiophene-2-carboxylate (CuTC) or copper (I) 3-methylsalicylate (CuMeSal), the palladium-catalyzed cross-coupling of thioalkyne derivatives with boronic acids affords functionalized alkynes in yields ranging from 39 to 91%. This coupling occurs efficiently under mild, nonbasic conditions with a wide variety of thioalkynes and boronic acids, providing a reaction complementary to the Sonogashira protocol.