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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Journal ArticleDOI
Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent
Esther Boess,Devarajulu Sureshkumar,Abhishek Sud,Cornelia Wirtz,Christophe Farès,Martin Klussmann +5 more
TL;DR: The effect of methanol to effectively stabilize the iminium ion was investigated and shown to be beneficial in an oxidative allylation reaction.
Journal ArticleDOI
Wherefore Art Thou Copper? Structures and Reaction Mechanisms of Organocuprate Clusters in Organic Chemistry.
Eiichi Nakamura,Seiji Mori +1 more
TL;DR: This review will summarize first the general structural features of organocopper compounds and the previous mechanistic arguments, and then describe the most recent mechanistic pictures obtained through high-level quantum mechanical calculations for three typical organocuprate reactions, carbocupration, conjugate addition, and S(N)2 alkylation.
Journal ArticleDOI
Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant.
Qi-Xiang Guo,Zhi-Jun Wu,Zhibin Luo,Quan-Zhong Liu,Jian-Liang Ye,Shi-Wei Luo,L.-F. Cun,Liu-Zhu Gong +7 more
TL;DR: Kinetic studies, the cross-coupling reaction, and HRMS spectral studies on the reaction have been carried out and illustrate that two vanadium(V) species are both involved in catalysis and that the coupling reaction undergoes a radical-radical mechanism in an intramolecular manner.
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