Base-promoted tandem synthesis of 2-azaaryl indoline.

A novel tandem method to synthesize 2-azaaryl indoline promoted by LiN(SiMe 3 ) 2 from 2-azaaryl methyl amine and 2-fluoro benzyl bromides was developed. Mechanistic investigation indicated that this tandem cyclization was initiated by selective benzyl C-S N 2 substitution followed by an intramolecular S N Ar reaction. Diverse 2-azaaryl indoles could also be obtained via simple functional transformations.