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Yoshikai, N. : 2023 Science of Synthesis, 2022/5: Base-Metal Catalysis 1 DOI: 10.1055/sos-SD-238-00150
Base-Metal Catalysis 1

1.8 Copper-Catalyzed Aerobic Oxidation of Alcohols

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Editor: Yoshikai, N. 

Authors: Chatani, N. ; Chemler, S. R. ; Chen, P. ; Dai, H.-X. ; Delcaillau, T.; Fujihara, T. ; Huang, J. ; Iwabuchi, Y. ; Kennedy-Ellis, J. J. ; Ko, C.; Koh, M. J. ; Lee, B. C.; Li, Y.; Lin, L.; Liu, G. ; Ma, D. ; Morandi, B. ; Nakao, Y. ; Ouyang, Y. ; Pang, X.; Qing, F.-L. ; Ren, Y. ; Sasano, Y. ; Shang, Y. ; Shou, J.-Y.; Shu, X.-Z. ; Su, W. ; Tobisu, M. ; Wang, C. ; Xiong, T. ; Xu, H.; Yang, F.; Yoshida, T.; Zhu, S. 

Title: Base-Metal Catalysis 1

Print ISBN: 9783132453807; Online ISBN: 9783132453821; Book DOI: 10.1055/b000000441

1st edition © 2023 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

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

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

The oxidation of alcohols to carbonyl compounds is one of the most important reactions in organic synthesis. Owing to current environmental concerns, catalytic alcohol oxidation using molecular oxygen as the terminal oxidant has been actively investigated. Copper is frequently used as an aerobic oxidation catalyst in organic syntheses, as well as in biological systems. Co-catalysts acting in coordination with copper to promote the aerobic oxidation of alcohols have been extensively investigated, and in this context the use of nitroxyl radicals has been identified as a promising strategy. Through the efforts of many researchers, nitroxyl radical/copper catalyst systems that efficiently oxidize traditionally more challenging aliphatic alcohols under mild conditions have recently been discovered. Methods for the synthesis of esters, imines, nitriles, amides, and imides by nitroxyl radical/copper-catalyzed aerobic alcohol oxidation in the presence of other alcohols, amines, and amides have also been developed. Nitroxyl radical/copper-catalyzed aerobic alcohol oxidation exhibits outstanding chemoselectivity, and efficiently converts alcohols bearing oxidation-prone functional groups that cannot be efficiently oxidized using conventional methods.

Key words

copper catalysis - alcohols - aerobic oxidation - nitroxyl radicals - nitroxides - cooperative catalysis - chemoselectivity - aldehydes - ketones - lactones - esters - imines - nitriles - amides - imides - amino alcohols - sulfides - dithianes
 
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