Aryl Nitro Reduction with Iron Powder or Stannous Chloride under Ultrasonic Irradiation

Authors

A. B. Gamble, University of Wollongong
James A. Garner, University of WollongongFollow
Christopher GordonFollow
S. M. J. O'Conner, University of Wollongong
Paul A. Keller, University of WollongongFollow

RIS ID

22172

Publication Details

This article was originally published as Gamble, AB, Garner, J, Gordon, CP, O'Conner, SMJ & Keller, PA, Aryl Nitro Reduction with Iron Powder or Stannous Chloride under Ultrasonic Irradiation, Synthetic Communications, 37, 2007, 2777-2786. Original journal article available here

Abstract

The selective reduction of aryl nitro compounds in the presence of sensitive functionalities, including halide, carbonyl, nitrile and ester substituents under ultrasonic irradiation at 35 kHz is reported in yields of 39-98%. Iron powder proved superior to stannous chloride with high tolerance of sensitive functional groups and high yields of the desired aryl amines in relatively short reaction times. Simple experimental procedure and purification also make the iron reduction of aryl nitro compounds advantageous over other methods of reduction.