高效钯催化的乙炔基乙醚氢化锡化反应。
Highly efficient palladium-catalyzed hydrostannation of ethyl ethynyl ether.
作者信息
Andrews Ian P, Kwon Ohyun
机构信息
Department of Chemistry & Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569, USA.
出版信息
Tetrahedron Lett. 2008 Dec 8;49(50):7097-7099. doi: 10.1016/j.tetlet.2008.09.147.
The palladium-catalyzed hydrostannation of acetylenes is widely exploited in organic synthesis as a means of forming vinyl stannanes for use in palladium-catalyzed cross-coupling reactions. Application of this methodology to ethyl ethynyl ether results in an enol ether that is challenging to isolate from the crude reaction mixture because of incompatibility with typical silica gel chromatography. Reported here is a highly efficient procedure for the palladium-catalyzed hydrostannation of ethyl ethynyl ether using 0.1% palladium(0) catalyst and 1.0 equiv of tributyltin hydride. The product obtained is a mixture of regioisomers that can be carried forward with exclusive reaction of the beta-isomer. This method is highly reproducible; relative to previously reported procedures, it is more economical and involves a more facile purification procedure.
钯催化的乙炔氢锡化反应在有机合成中被广泛应用，作为形成乙烯基锡烷的一种方法，用于钯催化的交叉偶联反应。将该方法应用于乙炔基乙醚时，会生成一种烯醇醚，由于与典型的硅胶柱色谱不兼容，很难从粗反应混合物中分离出来。本文报道了一种高效的方法，使用0.1%的钯(0)催化剂和1.0当量的三丁基氢化锡对乙炔基乙醚进行钯催化氢锡化反应。得到的产物是区域异构体的混合物，可以直接进行β-异构体的专一反应。该方法具有高度的可重复性；相对于先前报道的方法，它更经济，且纯化过程更简便。
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