The Development of a Scalable, Chemoselective Nitro Reduction

We have demonstrated a scalable chemoselective reduction of a nitro functional group in the presence of an aryl imine using (NH4)2S/EtOH or hydrogenation (Sponge Nickel) to afford the corresponding amino-imines in moderate to excellent yields. Other reducible groups such as aryl halides, styryl olef...

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Bibliographic Details
Published inOrganic process research & development Vol. 16; no. 10; pp. 1665 - 1668
Main Authors Gallagher, William P, Marlatt, Mark, Livingston, Robert, Kiau, Susanne, Muslehiddinoglu, Jale
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.10.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
STANNOUS CHLORIDE
SYSTEM
MILD
NITROARENES
HYDROGENATION
BIOLOGICAL EVALUATION
SELECTIVE REDUCTION
AROMATIC NITROCOMPOUNDS
EFFICIENT
RANEY-NICKEL
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Summary:We have demonstrated a scalable chemoselective reduction of a nitro functional group in the presence of an aryl imine using (NH4)2S/EtOH or hydrogenation (Sponge Nickel) to afford the corresponding amino-imines in moderate to excellent yields. Other reducible groups such as aryl halides, styryl olefins, and ether linkages survived as well.
ISSN:1083-6160
1520-586X
DOI:10.1021/op3002239