Journal ArticleDOI
Copper-Catalyzed Aerobic Oxidative C ? H Functionalizations: Trends and Mechanistic Insights
TLDR
This work has reported several recently reported Cu-catalyzed C-H oxidation reactions that feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II), and evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism.Abstract:
The selective oxidation of C-H bonds and the use of O(2) as a stoichiometric oxidant represent two prominent challenges in organic chemistry. Copper(II) is a versatile oxidant, capable of promoting a wide range of oxidative coupling reactions initiated by single-electron transfer (SET) from electron-rich organic molecules. Many of these reactions can be rendered catalytic in Cu by employing molecular oxygen as a stoichiometric oxidant to regenerate the active copper(II) catalyst. Meanwhile, numerous other recently reported Cu-catalyzed C-H oxidation reactions feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II). In some of these cases, evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism. Organometallic C-H oxidation reactions of this type represent important new opportunities for the field of Cu-catalyzed aerobic oxidations.read more
Citations
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Journal ArticleDOI
Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization
Journal ArticleDOI
Catalytic Functionalization of C(sp2) ? H and C(sp3) ? H Bonds by Using Bidentate Directing Groups
Guy Rouquet,Naoto Chatani +1 more
TL;DR: It would, therefore, appear that direct functionalization of substrates by activation of C-H bonds would eliminate the multiple steps and limitations associated with the preparation of functionalized starting materials.
Journal ArticleDOI
Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications
TL;DR: This Review comprehensively highlights recent advances in intra- and intermolecular C-H amination reactions utilizing late transition metal-based catalysts using mechanistic scaffolds and types of reactions.
Journal ArticleDOI
3d Transition Metals for C-H Activation.
Parthasarathy Gandeepan,Thomas Müller,Daniel Zell,Gianpiero Cera,Svenja Warratz,Lutz Ackermann +5 more
TL;DR: A comprehensive overview on first row transition metal catalysts for C-H activation until summer 2018 is provided.
Journal ArticleDOI
Mild metal-catalyzed C–H activation: examples and concepts
TL;DR: This review presents the current state of the art in this field and detail C-H activation transformations reported since 2011 that proceed either at or below ambient temperature, in the absence of strongly acidic or basic additives or without strong oxidants.
References
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Book ChapterDOI
Homogeneous Copper-Catalyzed Oxidations
TL;DR: A review of the role of copper containing active sites in metalloproteins that catalyze oxidation or oxygenation reactions in nature can be found in this paper, where the authors focus on the results obtained in catalysis and the mechanistic studies undertaken to support these results; therefore less emphasis is given to more fundamental coordination chemistry aspects of the Cu-complexes described as well as their spectroscopic characteristics.
Journal ArticleDOI
Organocuprate(iii) chemistry: synthesis and reactivity of amido, cyano, phosphido and thiolato ate complexes of copper(iii)
TL;DR: Lithium tetramethylcuprate(III) 1 reacts readily at -100 degrees C with appropriate sources of H(+) or X(+) (X = Br, I) to remove a methyl and in some cases incorporate the counterion to give stable complexes.
Journal ArticleDOI
Controlled copper-mediated chlorination of phenol rings under mild conditions.
Yufei Song,Gerard A. van Albada,Jinkui Tang,Ilpo Mutikainen,Urho Turpeinen,Chiara Massera,Olivier Roubeau,José Sánchez Costa,Patrick Gamez,Jan Reedijk +9 more
TL;DR: The very unusual case of copper-mediated chlorination of phenol rings under mild conditions at room temperature is reported and the magnetic susceptibility of the two compounds was investigated, revealing either very strong or strong antiferromagnetic dominant interactions among the CuII ions for 1 and 2.
Journal ArticleDOI
Perylenequinone natural products: total syntheses of the diastereomers (+)-phleichrome and (+)-calphostin D by assembly of centrochiral and axial chiral fragments.
TL;DR: Three routes were evaluated to establish the C7,C7'-stereochemistry, in which the successful route involved a double epoxide alkylation with a complex axial chiral biscuprate, which allowed the synthesis of the unnatural isomers of calphostin D and phleichrome for assessment in biological systems.
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