碘催化的2-炔基苯胺与二硒醚的亲电环化反应

Iodine-catalyzed Electrophilic Cyclization of 2-Alkynylanilines with Diselenides

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.

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 12 and toluene, a variety of 2-alkynylanilines selectively underwent the electrophilie eyclization 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.