NaHS·nH2O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles

Chem Commun (Camb). 2018 Nov 8;54(90):12730-12733. doi: 10.1039/c8cc07599a.

Abstract

An efficient method for constructing 2-acyl-3-aminoindoles from methyl ketones and 2-aminobenzonitriles is described, in which NaHS·nH2O is used as a novel umpolung reagent for the first time in organic synthesis. Mechanistic studies revealed that the key step involved an Eschenmoser sulfide contraction reaction.