Switchable synthesis of 3-aminoindolines and 2′-aminoarylacetic acids using Grignard reagents and 3-azido-2-hydroxyindolines

Abstract

The switchable synthesis of 3-aminoindolines and 2′-aminoaryl acetic acids from the same substrates, 3-azido-2-hydroxyindolines, was developed through denitrogenative electrophilic amination of Grignard reagents. The key to success is the serendipitous discovery that the reaction conditions, including solvents and reaction temperature, can affect the chemoselectivity. It is noteworthy that isotope-labeling experiments revealed the occurrence of the aziridine intermediate in the production of 2′-aminoaryl acetic acids.