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引用次数: 0
摘要
尽管硫醇的脱硫是一个非常重要的课题,并受到了极大的关注,但大多数工作都集中在硫醇的氢脱硫上。在这项工作中,我们描述了硫醇的亲核取代脱硫过程。这一过程在 Ph3P/ICH2CH2I 系统的促进下迅速发生,并可扩展至多种亲核物。值得注意的是,游离胺可用作亲核物来合成各种仲胺和叔胺。这种方法可容忍多种官能团,包括胺化反应中的羟基。苄基硫醇的反应性特别强,可在室温下 15 分钟内完全转化。虽然烷基硫醇的反应活性较低,但它们也可以在 70 °C 的反应温度下顺利转化过夜。
Desulfurization of Thiols for Nucleophilic Substitution
Although the desulfurization of thiols is a topic of great importance and has received significant attention, most efforts have focused on the hydrodesulfurization of thiols. In this work, we describe the desulfurization of thiols for nucleophilic substitution. This process occurs rapidly, promoted by the Ph3P/ICH2CH2I system, and can be extended to a wide range of nucleophiles. Notably, free amines can be employed as nucleophiles to synthesize various secondary and tertiary amines. This method tolerates a wide array of functional groups, including hydroxyl groups in amination reactions. Benzyl thiols are particularly reactive and can be completely converted at room temperature within 15 min. Although alkyl thiols show lower reactivity, they can also be converted smoothly at a reaction temperature of 70 °C overnight.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.