Abstract:

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.

Key words: Iodine, 2-Alkynylaniline, Diselenide, Electrophilic cyclization