1.3 Copper-Catalyzed Alkene Difunctionalization
Book
Editor: Yoshikai, N.
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
Abstract
![](https://www.thieme-connect.de/media/10.1055-b000000441/thumbnails/a_225nyd.jpg)
Alkene difunctionalization is a classic molecular transformation in organic synthesis, enabling the production of more-complex molecules from simple hydrocarbon-derived feedstocks. Alkene difunctionalizations catalyzed by copper complexes offer potentially more-sustainable protocols compared to those catalyzed by more-precious or -toxic metals. This chapter summarizes important recent advancements in the field, especially in the area of asymmetric catalysis. A number of copper-catalyzed intramolecular and intermolecular alkene difunctionalizations for the synthesis of cyclic and acyclic chiral amines and ethers, and related compounds, are presented. The reactions include alkene and/or diene hydroamination, hydroetherification, carboamination, carboetherification, diamination, oxyamination, and dicarbofunctionalization. Many of the reaction mechanisms involve a radical component either in the first or second bond-forming event. The ability of copper to engage with radicals in bond-forming events, including enantioselective ones, is a valuable aspect of many of these reactions.
Key words
alkenes - amines - amino alcohols - aminooxygenation - aziridines - carboamination - carboetherification - copper catalysis - diamination - dicarbofunctionalization - dienes - difunctionalization - enantioselective - ethers - hydroamination - hydroetherification - indolines - lactams - lactones - pyrrolidines - radicals- 20 Wang F.-L, Dong X.-Y, Lin J.-S, Zeng Y, Jiao G.-Y, Gu Q.-S, Guo X.-Q, Ma C.-L, Liu X.-Y. Chem 2017; 3: 979
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