Departamento de Química Orgánica e Inorgánica e InstitutoUniversitario de Química Organometálica Enrique Moles, Universidad de Oviedo c/ Julián Clavería 8, Oviedo 33007, Spain.
Angew Chem Int Ed Engl. 2011 Aug 8;50(33):7486-500. doi: 10.1002/anie.201007961. Epub 2011 Jul 11.
Tosylhydrazones are useful synthetic intermediates that have been used in organic chemistry for almost 60 years. The recent discovery of a palladium-catalyzed cross-coupling reaction involving a tosylhydrazone coupling partner has triggered renewed interest in these reagents. This reaction shows nearly universal generality with regard to the hydrazone and can be employed for the preparation of polysubstituted alkenes. In the course of this research, novel metal-free C-C and C-O bond-forming reactions have been discovered. Since tosylhydrazones are readily prepared from carbonyl compounds, these transformations offer new synthetic opportunities for the unconventional modification of carbonyl compounds. This Minireview discusses all of these new reactions of a classic reagent.
对甲苯磺酰腙是一种有用的合成中间体，在有机化学中已经使用了近 60 年。最近发现的钯催化交叉偶联反应涉及对甲苯磺酰腙偶联试剂，这重新引起了人们对这些试剂的兴趣。该反应对腙具有几乎普遍的适用性，可用于制备多取代烯烃。在这项研究过程中，发现了新型的无金属 C-C 和 C-O 键形成反应。由于对甲苯磺酰腙可以很容易地从羰基化合物制备，因此这些转化为羰基化合物的非常规修饰提供了新的合成机会。这篇综述讨论了经典试剂的所有这些新反应。
