A facile synthesis of N,3-disubstituted indoles and 3-hydroxyl indolines via an intramolecular SNAr of fluorinated amino alcohols

In this Letter, we describe a practical and highly versatile method for the preparation of N,3-disubstituted indoles and 3-hydroxyl indolines. This synthetic strategy relies on an epoxide-opening followed by an intramolecular SNAr of the resulting fluoroaryl amino alcohols. The reaction afforded 3-hydroxyl indolines when carried out at lower temperature for the derivatives bearing multi-fluorine substituents at the aromatic ring.

Graphical abstractIn this Letter, we describe a practical and highly versatile method for the preparation of N,3-disubstituted indoles and 3-hydroxyl indolines. This synthetic strategy relies on an epoxide opening followed by an intramolecular SNAr of the resulting fluoroaryl amino alcohols. The reaction afforded 3-hydroxyl indolines when carried out at lower temperature for the derivatives bearing multi-fluorine substituents at the aromatic ring.Download full-size image