2.7 Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N -Oxides to Amines
Buch
Herausgeber: de Vries, J. G.
Titel: Catalytic Reduction in Organic Synthesis 2
Print ISBN: 9783132406261; Online ISBN: 9783132406308; Buch-DOI: 10.1055/b-005-145235
1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie
Science of Synthesis Reference Libraries
Übergeordnete Publikation
Titel: Science of Synthesis
DOI: 10.1055/b-00000101
Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Koch, G.; Molander, G. A.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Typ: Mehrbändiges Werk
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.
Schlüsselwörter
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- 2 Dixon DJ, Pando Morejón O, In Comprehensive Organic Synthesis, 2nd ed.. Knochel P, Molander GA. Elsevier; Amsterdam 2014. Vol. 8, p 479.
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