Direct Amidation of Carboxylic Acids with Nitroarenes

J Org Chem. 2019 Nov 1;84(21):13922-13934. doi: 10.1021/acs.joc.9b02068. Epub 2019 Oct 17.

Abstract

N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium salt for one-pot amidation, without the need for isolation of the corresponding synthetic intermediates. Furthermore, the ease of preparation and workup allow the quick and efficient synthesis of a wide range of N-aryl amides, including several amide-based druglike and agrochemical molecules.

Publication types

  • Research Support, Non-U.S. Gov't