Iridium(III)-Catalyzed Regioselective C7-Amination of N-Pivaloylindoles with Sulfonoazides

J Org Chem. 2016 Nov 4;81(21):10476-10483. doi: 10.1021/acs.joc.6b01856. Epub 2016 Sep 13.

Abstract

Direct C7-amination of N-pivaloylindoles has been achieved using a combination of [Cp*IrCl2]2, AgNTf2, and AgOAc as the catalyst and sulfonoazides as the nitrogen source. The reaction proceeded at room temperature to 80 °C to afford 7-sulfonamidoindoles in good to excellent yields. The reaction is broadly applicable to the C7-amination of a wide variety of 3-, 4-, 5-, and 6-substituted N-pivaloylindoles with either alkyl or aryl sulfonoazides.

Publication types

  • Research Support, Non-U.S. Gov't