Base-promoted tandem synthesis of 2-azaaryl indoline

Abstract

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-S_N2 substitution followed by an intramolecular S_NAr reaction. Diverse 2-azaaryl indoles could also be obtained via simple functional transformations.