Synthesis and reactivity of electron poor allenes: formation of completely organic frustrated Lewis pairs
作者:David Palomas、Sigrid Holle、Blanca Inés、Hans Bruns、Richard Goddard、Manuel Alcarazo
DOI:10.1039/c2dt30195d
日期:——
The synthesis of several electron poor allenes bearing electron withdrawing substituents is described and their use as Lewis acids in the field of frustrated Lewis pair (FLP) chemistry reported. At room temperature the combination of N-heterocyclic carbenes (NHC) with the allenes under study invariably afforded the corresponding Lewis adducts; however, at −78 °C this reaction is in most of the cases inhibited and kinetically induced organic FLPs are formed. Under these conditions the activation of S–S bonds in disulfides has been achieved in excellent yields.
描述了几种具有电子吸引取代基的电子贫乏丙烯合成,并报告了它们作为路易斯酸在受挫路易斯对(FLP)化学中的应用。在室温下,N-杂环卡宾(NHC)与研究中的丙烯的组合通常会形成相应的路易斯加合物;然而,在-78°C下,这一反应在大多数情况下受到抑制,并形成了动力学诱导的有机FLP。在这些条件下,成功实现了二硫化物中S–S键的激活,并取得了优良的产率。