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de Vries, J. G.: 2018 Science of Synthesis, 2017/6: Catalytic Reduction in Organic Synthesis 2 DOI: 10.1055/sos-SD-227-00139
Catalytic Reduction in Organic Synthesis 2

2.7 Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N-Oxides to Amines

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Editor: de Vries, J. G.

Authors: Ayad, T. ; Bagal, D.; Besson, M.; Bhanage, B. ; Ciszek, B.; Claver, C.; Cole-Hamilton, D.; Fleischer, I. ; Hinze, S.; Ikariya, T.; Junge, K.; Kalck, P.; Kamer, P.; Kayaki, Y. ; Llopis, Q.; Matsunami, A.; Monguchi, Y.; Peñafiel, I.; Phansavath, P.; Pinel, C.; Puylaert, P.; Ratovelomanana-Vidal, V. ; Sajiki, H.; Savini, A.; Shi, Y.; Steinfeldt, N.; Urrutigoity, M.

Title: Catalytic Reduction in Organic Synthesis 2

Print ISBN: 9783132406261; Online ISBN: 9783132406308; Book DOI: 10.1055/b-005-145235

1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Koch, G.; Molander, G. A.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

Various catalytic strategies are discussed for the reduction of both aromatic and aliphatic nitro functionalities to the corresponding amines, including homogeneous and heterogeneous (transfer) hydrogenations, as well as the water–gas shift reaction. Chemoselectivity with respect to other reducible moieties (carbonyls, alkenes, alkynes) and hydrodehalogenation is taken into account. The isolation of azobenzenes, N-substituted hydroxylamines, and oximes, which are typically considered intermediates or byproducts in nitro reductions, is included as well. Finally, developments in the deoxygenation of N-oxides are addressed briefly.

Key words

nitroaromatics - nitroaliphatics - reduction - deoxygenation - N-oxides - hydrogenation - transfer hydrogenation - water–gas shift reaction - anilines - amines - azobenzenes - N-substituted hydroxylamines - oximes - pyridines - chemoselectivity - scale-up - homogeneous catalysis - heterogeneous catalysis
 
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