Base-promoted tandem synthesis of 2-azaaryl indoline

A novel tandem method to synthesize 2-azaaryl indoline promoted by LiN(SiMe3)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-SN2 substitution followed by an intramolecular SNAr reaction. Diverse 2-azaaryl indoles could also be obtained via simple functional transformations. A novel strategy involving base-promoted tandem SN2 substitution and intramolecular SNAr addition from 2-azaaryl methyl amine and ortho-fluoro benzyl bromide was designed.