Pd-Catalyzed Silicon Hydride Reductions of Aromatic and Aliphatic Nitro Groups

Ronald J. Rahaim, Jr. and Robert E. Maleczka, Jr.*
Department of Chemistry, Michigan State University, East Lansing, Michigan 48824
Org. Lett., 2005, 7 (22), pp 5087–5090
DOI: 10.1021/ol052120n
Publication Date (Web): September 29, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mMaleczka@cem.msu.edu

Abstract

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Room-temperature reduction of aromatic nitro groups to amines can be accomplished in high yield, with wide functional group tolerance and short reaction times (30 min) using a combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS). Replacing PMHS/KF with triethylsilane allows aliphatic nitro groups to be reduced to their hydroxylamines.

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History

  • Published In Issue October 27, 2005
  • Received September 2, 2005

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