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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 16
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Original Articles

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

Allan B. Gamble Department of Chemistry, University of Wollongong, Wollongong, Australia
,
James Garner Department of Chemistry, University of Wollongong, Wollongong, Australia
,
Christopher P. Gordon Department of Chemistry, University of Wollongong, Wollongong, Australia
,
Sean M. J. O'Conner Department of Chemistry, University of Wollongong, Wollongong, Australia
&
Paul A. Keller Department of Chemistry, University of Wollongong, Wollongong, AustraliaCorrespondence[email protected]
Pages 2777-2786 | Received 10 Jan 2007, Published online: 14 Aug 2007
 
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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.

Acknowledgments

A. B. G. thanks the Australian government for an Australian Postgraduate Award, AVEXA Limited for financial support, and the Centre for Medicinal Chemistry and Pharmacology, UOW, for financial support.

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