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使用α-氧代烯酮二硫缩醛作为构建块,通过区域和立体选择性合成多取代烯烃和共轭二烯。

Regio- and stereoselective synthesis of multisubstituted olefins and conjugate dienes by using α-oxo ketene dithioacetals as the building blocks.

机构信息

Dalian Institute of Chemical Physics, Chinese Academy of Sciences (CAS), 457 Zhongshan Road, Dalian, Liaoning 116023, China.

出版信息

Org Lett. 2011 Aug 19;13(16):4272-5. doi: 10.1021/ol201620g. Epub 2011 Jul 15.

Abstract

An efficient palladium(0)-catalyzed, Cu(I)-mediated synthetic route to trisubstituted olefins and conjugate dienes has been developed via oxo directing Liebeskind-Srogl cross-coupling reactions of gem-dihaloolefin-type α-oxo ketene dithioacetals with aryl and alkenylboronic acids. The synthetic protocol has demonstrated rare examples of transition-metal-promoted transformations of ketene dithioacetals, providing a novel route to highly functionalized conjugate dienes.

摘要

通过偕二卤代烯烃型α-氧代烯酮二硫代缩醛与芳基和烯基硼酸的氧导向 Liebeskind-Srogl 交叉偶联反应,开发了一种高效的钯(0)催化、铜(I)介导的三取代烯烃和共轭二烯的合成途径。该合成方案证明了烯酮二硫代缩醛的过渡金属促进转化的罕见实例,为高度官能化的共轭二烯提供了新的途径。

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