Prokopcová Hana, Kappe C Oliver
Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, 8010 Graz, Austria.
Angew Chem Int Ed Engl. 2009;48(13):2276-86. doi: 10.1002/anie.200802842.
Although a plethora of highly selective and reliable methods for the construction of C-C bonds are known to organic chemists, there is growing interest in the development of new protocols that offer different or orthogonal reactivity to that of existing methods. In 2000, Liebeskind and Srogl described a mechanistically unprecedented transition-metal-catalyzed cross-coupling of thioesters with boronic acids to produce ketones under neutral conditions. This desulfitative cross-coupling process is catalytic in palladium(0), stoichiometric in copper(I), and applicable to a range of organosulfur derivatives and nucleophilic organometallic reagents. In this Minireview, we highlight recent applications of this intriguing cross-coupling reaction in modern organic synthesis, with an emphasis on cases in which traditional methods for C-C bond formation have failed.
尽管有机化学家们已经熟知大量用于构建碳-碳键的高选择性且可靠的方法，但人们对开发具有与现有方法不同或正交反应性的新方案的兴趣与日俱增。2000年，利贝斯金德（Liebeskind）和施罗格（Srogl）描述了一种在机理上史无前例的过渡金属催化硫酯与硼酸的交叉偶联反应，该反应能在中性条件下生成酮。这种脱硫交叉偶联过程以钯(0)为催化剂，以化学计量的铜(I)参与反应，并且适用于一系列有机硫衍生物和亲核有机金属试剂。在本综述中，我们重点介绍了这种有趣的交叉偶联反应在现代有机合成中的最新应用，尤其着重于传统碳-碳键形成方法失效的情况。
