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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, Email:

R. J. Rahaim, R. E. Maleczka, Jr., Org. Lett., 2005, 7, 5087-5090.

DOI: 10.1021/ol052120n (free Supporting Information)

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Palladium-catalyzed reduction of aromatic nitro groups to amines can be accomplished in high yield, with wide functional group tolerance and short reaction times at r.t. using aqueous potassium fluoride and polymethylhydrosiloxane (PMHS) for aromatic nitro groups. Aliphatic nitro compounds are reduced to the corresponding hydroxylamines using triethylsilane instead of PMHS/KF.

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Key Words

Reduction of nitro compounds, Polymethylhydrosiloxane, Triethylsilane

ID: J54-Y2005-1800