Synthesis of indoles via domino reaction of 2-fluorotoluenes and nitriles.

Indoles are essential heterocycles in medicinal chemistry and, therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2-aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical and transition metal-free assembly of 2-arylindoles. Simply combining readily available 2-fluorotoluenes, nitriles, LiN(SiMe3)2 and CsF enables generation of a diverse array of indoles (38 examples, 48-92% yield). A range of substituents can be introduced into each position of the indole backbone (C-4 to C-7, and aryl groups at C-2), providing handles for further elaboration.