碘催化的2-炔基苯胺与二硒醚的亲电环化反应

研究了碘催化的2-炔基苯胺与二硒醚的亲电环化反应. 结果表明, 在碘单质(0.2 mmol)、 2-炔基苯胺(0.2 mmol)、 二硒醚(0.1 mmol)和甲苯(2 mL)共存体系中, 反应温度为110℃时, 2-炔基苯胺与二硒醚能发生亲电环化反应, 生成相应的3-硒取代吲哚化合物, 产率为中等到良好. 该反应在无金属催化的条件下进行, 为合成官能团吲哚提供了一种新途径.

Iodine-catalyzed Electrophilic Cyclization of 2-Alkynylanilines with Diselenides

Indoles, particularly 3-selenenylindoles, are important compounds found in a wide range of biologically active compounds and natural products, as well as are useful building blocks in organic synthesis. For the reasons, a new and efficient method for the selective synthesis of 3-selenenylindoles was developed by electrophilic iodocyclization of 2-alkynylanilines with diselenides. In the presence of I2 and toluene, a variety of 2-alkynylanilines selectively underwent the electrophilic cyclization with diselenides leading to the corresponding 3-selenenylindoles in moderate to excellent yields. Importantly, these reactions were conducted under metal-free conditions, and will open a new door to functionalized indoles synthesis.