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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-227-00073
Catalytic Reduction in Organic Synthesis 2

2.4 Hydrogenolysis of Aryl Ketones and Aldehydes, Benzylic Alcohols and Amines, and Their Derivatives

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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

This chapter provides an overview of the hetero- and homogeneous metal-catalyzed hydrogenolysis of C=O, C–O, and C–N bonds at benzylic positions. This reaction constitutes an atom- and waste-economic alternative to traditional defunctionalization methods. It has found numerous applications in organic synthesis, including in the removal of protecting groups from alcohols and amines. Moreover, its role in the valorization of biomass feedstocks is being intensely investigated.

Key words

hydrogenolysis - reduction - defunctionalization - deoxygenation - deprotection - aryl ketones - benzaldehydes - benzylic alcohols - benzylic amines - hydrogen - formic acid - palladium - nickel - ruthenium - cobalt - molybdenum - rhodium
 
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