Université Paris-Sud, CNRS, BioCIS-UMR 8076, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.-B. Clément, Châtenay-Malabry, F-92296, France.
J Org Chem. 2013 Jan 18;78(2):445-54. doi: 10.1021/jo3023268. Epub 2013 Jan 3.
The reactivity of sterically hindered N-tosylhydrazones 2 featuring ortho/ortho'-substituents on the aromatic ring with various ortho-, meta-, and para-substituted aryl halides 3 was investigated. To accomplish successfully this challenging coupling, fine-tuning of the reaction conditions were required. The newly established PdCl(2)(MeCN)(2)/Xphos/NaO-t-Bu/F-benzene system in a sealed tube is compatible with a broad spectrum of both coupling partners, regardless of their electronic and steric nature. This protocol has been applied successfully to the synthesis of a xanthene derivative.
研究了具有邻位/邻位'-取代基的空间位阻 N-对甲苯磺酰腙 2 与各种邻位、间位和对位取代的芳基卤化物 3 的反应性。为了成功完成这项具有挑战性的偶联反应，需要对反应条件进行精细调整。在密封管中使用新建立的 PdCl2(MeCN)2/Xphos/NaO-t-Bu/F-苯体系与广泛的偶联物兼容，无论它们的电子和空间性质如何。该方案已成功应用于香豆素衍生物的合成。
